bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of 2‐amino‐5,6‐dihydro‐4H‐1,3‐thiazines and related compounds by acid catalyzed cyclization of allylic isothiuronium salts
Authors: Cohen Noal , Banner Bruce L. 
Published: April 2009

AbstractSeveral allylic isothiuronium salts 6 have been shown to yield 4‐substituted 2‐amino‐5,6‐dihydro‐4H‐1,3‐thiazines (2; R3 = H) and the 2‐phenylimino compound 10 on exposure to trifluoroacetic acid or trifluoroacetic acid‐stannic chloride. The overall process constitutes a convenient transformation of readily available ketones or aldehydes 3 into the target hetero‐cycles. The scope and limitations of this approach are discussed in terms of carbenium ion intermediates (7). Whereas this method successfully led to the imidazo[2,l‐b][1,3]thiazine 13 (93% from 12), its application to the synthesis of 2‐amino‐2‐thiazolines (eg. 14→ 15) or imidazo‐[2,1‐b]thiazoles (eg. 16 → 17) was unsuccessful. The 2‐acetylimino derivatives 9 were found to be useful for purification of the 2‐aminothiazines.
Tetrazoles from N‐(4‐dimethylaminophenyl)nitrones and hydrogen azide
Authors: Moderhack Dietrich 
Published: April 2009

AbstractThe reaction of N‐(4‐dimethylaminophenyl)nitrones, 1, with hydrogen azide proceeds via three distinct pathways to give a mixture of two tetrazoles, 5 and 9, and a 2‐azido‐4‐dimethyl‐aminoaniline derivative, 6. The proportions largely depend on the electron‐withdrawing force resident in the function R attached to nitrone carbon. The formation of 5 constitutes a new synthetic approach to 1,5‐disubstituted tetrazoles.
[1] Benzofuro [2,3‐d] pyridazines II. Etude des benzofuropyridazones
Authors: De Sévricourt Michel Cugnon , Robba Max 
Published: April 2009

AbstractLa dihydro‐1,2 oxo‐1 [1] benzofuro [2,3‐d] pyridazine et la dihydro‐3,4 oxo‐4 [1] benzofuro [2,3‐d] pyridazine sont synthétisées par cyclisation de I'hydrazine avec des dérivés benzofuran‐niques earbonylés. Une autre voie d'accés, mettant en oeuvre la tétrabydro‐1,2,3,4 dioxo‐1,4 [1] benzofuro [2,3‐d] pyridazine et la tetrahydro‐1,2,3,4 oxo‐4 [1] benzofuro [2,3‐d] pyridazine, a été mise en oeuvre. La strueture d'une benzofuropyridazone‐4 nitrée sur l'homoeyele a été établie par application de l'effet Overhauser.
Recherches sur le benzofuranne, LVII. Sur une chloration inhabituelle de l'hétérocycle au cours de la réduction des (nitro‐4 phényl)‐2 ou ‐3 benzo‐furannes par le chlorure stanneux
Authors: Demerseman Pierre , Flad Geneviéve , Platzer Nicole , Royer Et René 
Published: April 2009

AbstractLes réductions des (nitro‐4 phényl)‐2 et (nitro‐4 phényl)‐3 benzofurannes par le chlorure stanneux en présence d'acide chlorhydrique fournissent non seulement les (amino‐4 phényl)‐2 et (amino‐4 phényl)‐3 benzofurannes attendus mais aussi les (amino‐4 phényl)‐2 chloro‐3 et (amino‐4 phényl)‐3 chloro‐2 benzofurannes dont les structures sont démontrées notamment par leurs spectres de rmn du 13C établis en comparaison de ceux des phényl‐2 et phényl‐3 benzofurannes. Ces chlorations parasites á la réduction precédent vraisemblablement d'un mécanisme radical aire.
Reaction of piperidine and morpholine with 2H‐pyran‐2‐ones, 2H‐thiopyran‐2‐ones, 2H‐pyran‐2‐thiones, and 2H‐thiopyran‐2‐thiones. A novel route to thiophene derivatives
Authors: El‐Kkoly Ibrahim El‐Sayed , Mishrikey Morcos Michael , Fuid‐Alla Hassan Mostafa 
Published: April 2009

AbstractThe reaction of piperidine or morpholine with 2H‐pyran‐2‐ones was found to give open chain δ‐oxoamides, while with 2H‐thiopyran‐2‐ones, thiophene derivatives were formed. For 2H‐pyran‐2‐thiones, either open chain δ‐oxothioamides or thiophene derivatives were obtained. From the 1 H nmr data of the pyran derivatives, the effect of the replacement of ring and carbonyl oxygens with sulphur on the chemical shift of the H‐3 proton could be studied.
The crystal and molecular structure of the cycloadduct from an activated carbodiimide and methyl isothiocyanate
Authors: Schaumann Ernst , Kausch Erwin , Klaska Karl‐Heinz , Klaska Rolf , Jarchow Otto 
Published: April 2009

AbstractThe crystal and molecular structures of the cycloadduct from isopropyl[α‐(dimethylthio‐carbamoyl)isopropyl]carbodiimide and methyl isothiocyanate were determined by single‐crystal X‐ray methods. The product was established to be 2‐(1‐isopropyl‐3,5‐dimethyl‐4,6‐dithioxo‐hexahydro‐1,3,5‐triazine‐2‐ylidenamino)‐N,N‐dimethylthioisoburyramide, in which contrary to expectations based on hybridisation the heterocyclic ring adopts a boat conformation.
Recherches sur le benzofuranne. LIX. Orientation de l'aroylation de l'éthyl‐2 benzofuranne selon la nature du chlorure d'aroyle utilise
Authors: Astoin Jacques , Demerseman Pierre , Platzer Nicole , Royer Et René 
Published: April 2009

AbstractContrairement aux chlorures d'alcanoyle et á certains chlorures d'aroylt: trés agressifs ou encombrés au voisinage du carbonyle qui réagissent exclusivement en 3 avec l'éthyl‐2 benzofuranne, la plupart des autres chlorures d'aroyles l'attaquent egalement en 6 et accessoirement en 4.
Synthesis of dimethoxybenz[g]isoquinolines
Authors: Menon C. S. , Zee‐Cheng Robert K.‐Y. , Cheng C. C. 
Published: April 2009

AbstractStobbe condensation of 2,3‐dimethoxybenzaldehyde with diethyl succinate, followed by reduction and cyclization, gave 3‐carbethoxy‐5,6‐dimethoxy‐l‐tetralone (7a). Subsequent reduction, aromatization and side chain conversion yielded the key intermediate 7,8‐dimethoxy‐2‐naphthalenecarboxaldehyde (8c). 6,7‐Dimethoxybenz[g]isoquinoline (1) was prepared from 8c via condensation with nitromethane, reduction, formylation, cyclization, and aromatization reactions; the isomeric 8,9‐dimethoxybenz[g]isoquinoline (2) was obtained by the condensation of 8c with the diethyl acetal of aminoacetaldehyde (12) followed by reduction, tosylation, cyclization and aromatization. The methiodides of both compounds were also prepared.
Synthesis of 1‐amino‐5‐phenyl‐4,5‐dihydro‐3H‐2‐benzazepines and the isomeric 2‐amino‐1‐benzazepines
Authors: Kukla Michael J. 
Published: April 2009

AbstractThe title amidines (1 and 2) were synthesized. A synthesis of lactam 10 free of isomeric 4 is described. An interesting rate difference in displacement of thiomethyl ether intermediates 5 and 11 with amines was observed.
2‐(Methylpyridyl or quinolyl)benz‐X‐azoles
Authors: Barni Ermanno , Savarino Piero 
Published: April 2009

AbstractIn view of the preparation of heterocyclic polymethine dyes, 2‐(methylpyridyl or quinolyl)‐benz‐X‐azoles were synthesized with the general reaction between carboxylic acids (or derivatives) and o‐bifunctional compounds. The electronic spectra and the methyl proton chemical shifts are briefly discussed.
Quaternization of 2‐aziridino‐5‐chlorobenzophenone, an efficient synthesis of medazepam
Authors: Mihalić M. , Šunjić V. , Kajfež F. , Žinić M. 
Published: April 2009

AbstractQuaternization of 2‐aziridino‐5‐chlorobenzophenone (1) with methyl iodide resulted in formation of 2‐(N‐β‐iodoethyl‐N‐methyl)aminobenzophenone (2), via an unstable quaternary compound. Rate constants for 1 → 2 conversion, as determined by an nmr method at 35 ± 0.1°, varied between 0.22 × 10−3 sec−1 in DMSO‐d6, and 0.95 × 10−6 sec−1 in methanol‐d4. Ammonolysis with hexamine, and subsequent cyclization afforded 7‐chloro‐l‐methyl‐5‐phenyl‐2,3‐dihydro‐lH‐1,4‐benzodiazepine (3, generic name medazepam) in 92% over‐all yield.
Condensation of o‐aminophenol and α‐dicarbonyl compounds. Part 2. Dibenzoxazolines
Authors: Belgodere E. , Bossio R. , Parrini V. , Pepino R. 
Published: April 2009

AbstractThe study of 2′‐aryl‐2,2′‐dibenzoxazolines (II), obtained together with 2‐hydroxy‐(2H)‐1,4‐benzoxazines (1) by condensation of o‐aminophenol with a series of phenylglyoxal derivatives, emphasized that these compounds are an equilibrium mixture of dibenzoxazolines and related tautomeric ketimine forms. This behaviour was widely investigated by ir, uv and pmr spectroscopy. J. Heterocyclic Chem., 14, 957 (1977)
Cycloadditions dipolaires 1,3. XXIX. Addition de deux esters nitroniques isomères à diverses défines. Etude de la régiosélectivitè et du mode d'approche du dipolarophile par le dipôle
Authors: Grée René , Carrié Robert 
Published: April 2009

AbstractLes cycloadditions dipolaires 1,3 de deux esters nitroniques isomères géométriques à diverses oléfines mono, di et trisubstituées sont áetudiées. Pour chaque réaction, rorientation e la cycloaddition est unique et conforme aux prévisions théoriques. Les modes d'approche de ces dipolarophiles par les deux esters nitroniques sont établis dans la plupart des cas. IIs sont discutès a l'aide de propriétés des orbitales frontières des réactifs. J. Heterocyclic Chem., 14, 965 (1977)
Synthesis of a tetraazacyclotetradecadiene and a pentaazacyclotetradecatriene
Authors: Griffiths David , Hull Roy 
Published: April 2009

AbstractUseful procedures for preparing a novel tetraazacyclotetradecadiene and a pentaazacyclotetradecatriene are reported. J. Heterocyclic Chem., 14, 1097 (1977)
The reaction of indole and the indole grignard reagent with phosgene. A facile synthesis of indole‐3‐carboxylic acid derivatives
Authors: Bergman Jan , Carlsson René , Sjöberg Birger 
Published: April 2009

AbstractIndole‐3‐carboxylic acid (as well as indole‐3‐glyoxylic acid) derivatives are readily prepared from indoles (including oxindoles) and phosgene (oxalyl chloride), respectively. The interaction of these reagents with the indole Grignard reagent afforded several products including the cyclo‐tetramers, 21 and 30. Indolo‐fused heterocycles can be readily prepared from the reaction of phosgene (or oxalyl chloride) with suitable reactants. Thus e.g., phosgene and 2‐(2‐hydroxy‐phenyl)‐N‐methylindole readily gave 5,6‐dihydro‐11‐methyl‐6‐oxobenzo[a]pyrano[4,3‐b] indole (33).
Synthesis of 4‐substituted 1,4‐benzodiazepine‐3,5‐diones
Authors: Stavropoulos G. , Theodoropoulos D. 
Published: April 2009

AbstractSynthetic routes leading to the preparation of 4‐substituted 1,4‐benzodiazepine‐3,5‐diones are described. Thus, 2‐carbobenzoxyaminobenzoic acid was converted to its p‐nitrobenzyl ester (I) and the decarbobenzoxylated product (II) gave, with ethyl α‐bromoacetate, N‐(2‐carboxy p‐nitrobenzylate)phenylglycine ethyl ester (III). The latter was hydrogenolyzed to N‐(2‐car‐boxy)phenylglycine ethyl ester (IV), which was coupled with benzylamine to give N‐(2‐carboxy‐benzylamido)phenylglycine ethyl ester (VIa). Saponification of VIa afforded N‐(2‐carboxy‐benzylamido)phenylglycine (VIIa) which was cyclized with DCCI to produce 4‐benzyl‐2H‐1,4‐benzodiazepine‐3,5(lH,4H)dione (VIIIa). Alternatively, 2‐nitro‐N‐phenylbenzamide (Xb) was reduced to 2‐amino‐N‐phenylbenzamide (XIb) which was converted to N‐(2‐carboxanih'do)‐phenylglycine ethyl ester (VIb). The latter was converted to 4‐phenyl‐2H‐1,4‐benzodiazepine‐3,5(1H,4H)dione (VIIIb) in an analogous fashion described for VIIIa.
Synthesis of 2‐amino‐3‐carbethoxy‐1‐hydroxyindoles
Authors: Munshi K. L. , Kohl H. , De Souza N. J. 
Published: April 2009

AbstractA general method is described for the synthesis of 2‐amino‐3‐carbethoxy‐l‐hydroxyindoles by the reductive cyclization of 2‐nitrophenylcyanoacetates using zinc and acetic acid at temperatures of 15–28°.
Synthesis of 2,4,6‐trinitrophenyl derivatives of heterocyclic compounds
Authors: Dacons Joseph C. , Sitzmann Michael E. 
Published: April 2009

AbstractThe preparation of 2,4,6‐trinitrophenyl (picryl) derivatives of triazine, pyrimidine, thiophene, furan, thiazole, 1,3,4‐oxadiazole and 1,3,4‐thiadiazole is described. The picryl derivatives are prepared by the Ullmann reaction and by cyclization reactions to form the heterocyclic ring.
Novel fused‐ring derivatives of 2‐methyl‐3‐o‐tolyl‐4(3H)quinazolone; Quinazolino [3,2‐a] [1,4] benzodiazepines
Authors: Harrison D. R. , Kennewell P. D. , Taylor J. B. 
Published: April 2009

AbstractThe synthesis of some quinazolino[3,2‐a][1,4]benzodiazepines from 2‐bromomethyl‐3‐o‐carbomethoxyphenyl‐4(3H)quinazolone is described. Alkylation and acylation of N‐6 led to a series of novel derivatives of this ring system.
Novel bicyclo[2.2.2]octanyl‐1,4‐benzodiazepinones. Their syntheses and rearrangement to bicyclooct‐2‐enylbenzimidazoles
Authors: Fairhurst J. , Horwell D. C. , Timms G. H. 
Published: April 2009

AbstractThe synthesis of the novel bicyclo[2.2.2]octanyl[1,4]benzodiazepinone ring system (IV) and its facile acid catalysed rearrangement to the corresponding bicyclo[2.2.2]oct‐2‐enylbenzirnid‐azole system (IX) is described.
The synthesis and spectra of new (E)‐(trans) and (Z)‐(cis)‐1‐alkyl‐2‐aryl (alkyl) ‐ 3 ‐aroylaziridines
Authors: Tarburton Philip , Wolpa Lori J. , Loerch Robert K. , Folsom Thomas L. , Cromwell Norman H. 
Published: April 2009

AbstractThe synthetic scope of the reaction of primary amines with α,β‐dibromochalones to form aroylaziridines is explored and found to require at least one hydrogen on the α‐carbon of the amine. Fourteen new epimeric l‐alkyl‐2‐aryl(alkyl)‐3‐aroylaziridines are synthesized accordingly. Next, representative aroylaziridines are investigated by infra‐red spectroscopy in solvents of ambient polarity to assess the relative populations of the gauche and cisoid conformers present in the (Z)‐(cis) series.
Synthesis of some 7‐α‐carboxyethyl‐1,3‐dihydro‐(2H)‐1,4‐benzodiazepin‐2‐ones
Authors: Žinić M. , Kolbah D. , Blažević N. , Kajfež F. , Šunjić V. 
Published: April 2009

Abstract1,4‐Benzodiazepin‐2‐ones possessing an α‐carboxyethyl group in 7‐position (21‐25) were prepared from a key compound, 2‐amino‐5‐α‐carboxyethylbenzophenone (8) or from its O‐benzyl derivative 14, using methods developed previously. An optimized route to 8 starting from 2‐nitro‐5‐chlorobenzophenone (1), as well as some unsuccessful attempts are described. Compound 8 was deaminated into racemic α‐(3‐benzoyl)‐phenylpropionic acid (9), a well‐known antiinflammatory agent.
The diazotization of 1‐aminophenazine
Authors: Olson Edwin S. 
Published: April 2009

AbstractAn investigation of why 1‐aminophenazine fails to form a diazonium salt which will couple with β‐naphthol revealed that the phenazine‐1‐diazonium cation reacts rapidly with water to give l‐diazo‐2(lH)phenazinone (1), whose coupling ability has been demonstrated to be very weak. A similar reaction occurred with 2‐aminophenazine.
A convenient synthesis of 2‐chromonecarboxylic acids
Authors: Pifferi Giorgio , Gaviraghi Giovanni , Pinza Mario , Ventura Paolo 
Published: April 2009

AbstractKnoevenagel condensation of the β‐ketosulfinyl intermediate II with butyl glyoxylate afforded the butyl 2‐hydroxy‐4‐(2‐hydroxyphenyl)‐3‐methylsulfinyl‐4‐oxobutyrates (III). Compounds III are versatile intermediates for the synthesis of either 2‐chromonecarboxylates (V) or 2‐carboxy‐methylene‐3‐coumaranone esters (VII).
Synthesis of Bi‐ and tridentate imidazole ligands
Authors: Sundberg Richard J. , Mente Donald C. , Yilmaz Ibrahim , Gupta Goutam 
Published: April 2009

AbstractA number of imidazole derivatives were prepared in the course of studying the limits of carbon‐metal bond formation in complexes of imidazole with first‐row transition metals. Seven of the compounds were new. The 4‐ and 5‐methyl and 4,5‐dimethyl derivatives of l‐(2‐pyridyl)‐imidazole were prepared by reaction of the appropriate imidazole with 2‐bromopyridine. Alkylation of imidazole, 4,5‐dimethylimidazole, and benzimidazole with 2‐chloromethylpyridine gave a series of 1‐(2‐pyridylmethyl)imidazoles. 1‐(2,3‐Diaminopropyl)imidazole was prepared in six steps via a Gabriel sequence.
Syntheses of “oxidized” hemopyrrole and kryptopyrrole: Porphyric monopyrroles
Authors: Wooldridge T. A. , Lightner D. A 
Published: April 2009

AbstractStraightforward, short synthetic procedures have been developed to produce gram quantities of 4,5‐dimethyl‐3‐ethyl‐5‐hydroxy‐3‐pyrrolin‐2‐one (1) and 3,5‐dimethyl‐4‐ethyl‐5‐hydroxy‐3‐pyrrolin‐2‐one (2), which are, respectively, the oxidized hemopyrrole and kryptopyrrole factors associated with psychiatric and prophyric disorders.
Stacked double‐macrocyclic ligands III. Spectral properties of cofacial diporphyrins as a function of the inter‐chromophore separation
Authors: Chang C. K. 
Published: April 2009

AbstractThree homologous cofacial diporphyrins that have interplanar distances ranging from 6.4Å to 4.2Å have been synthesized. Their absorption and emission spectra revealed strong exciton coupling in the diporphyrin. Magnesium complexes of diporphyrins were studied and their application as a model for P700 photoactive center was discussed.
Reaction of vinyl ketoximes with N‐bromosuccinimide. Synthesis of isoxazoles and 4‐bromoisoxazolines
Authors: Hansen John F. , Strong Scott A. 
Published: April 2009

AbstractThe reaction of some selected α,β‐unsaturated oximes with N‐bromosuccinimide gave isoxazoles or 4‐bromoisoxazolines in moderate to good yields.
1H‐pyrrolo[3,2‐c]pyridin‐4,6(5H,7H)dione(3,7‐dideazaxanthine)
Authors: Schneller S. W. , Hosmane R. S. 
Published: April 2009

AbstractA facile chemical synthesis of 1H‐pyrrolo[3,2‐c]pyridin‐4,6(5H,7H)dione (3,7‐dideazaxanthine) has been accomplished from ethyl 3‐ethoxycarbonylpyrrole‐2‐acetate.
An improved synthesis of 3‐deazaeytosine, 3‐deazauracil, 3‐deazacytidine, and 3‐deazauridine
Authors: Dan Cook P. , Day Robert T. , Robins Roland K. 
Published: April 2009

Abstract3‐Dcazacytosine (4‐amino‐2‐pyridone, 3), 3‐doazauracil (4‐hydroxy‐2‐pyridone, 5), 3‐deaza‐cytidine (4‐amino‐1‐β‐D‐ribofuranosyl‐2‐pyridonc, 9), and 3‐deazauridine (4‐hydroxy‐1‐β‐D‐ribo‐furanosyl‐2‐pyridone, 11) were prepared in high overall yields from 1‐methoxy‐1‐buten‐3‐yne (1). Ethyl 3,5,5‐triethoxy‐3‐pentenoate (2), obtained from acylatioti of 1 with diethyl carbonate and subsequent in situ conjugate addition of ethoxide, was cyelized with ammonia to provide 3. Diazotization of 3 and subsequent in situ hydroxydediazotization afforded 5. Nucleoside 9 was obtained from the stannic chloride‐catalyzed condensation of bis‐trimethylsilylated 3 and 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose (7), followed by ammonolysis of the blocking groups. Diazotization of 9 and subsequent in situ hydroxydediazotization afforded nucleosidc 11.
Etude expérimentale et théorique de la substitution de N‐méthyl‐halogéno‐triazoles‐1,2,4 par les réactifs nucléophiles
Authors: Maury Georges , Fkih‐Tétouani Souad , Arriau Jean , Sauvaǐtre Henri , Bernardini Antoine 
Published: April 2009

AbstractL'étude cinétique de la substitution des N‐méthyl‐halogénotriazoles‐1,2,4 isoméres par la pipéridine et l'ion méthoxyde rnontre que l'isomère méthyl‐1 halogéno‐5 est plus réactif que lisomère mèthyl‐4 halogéno‐3, le moins réactif étant l'isomère mèthyl‐1 halogéno‐3. L'applica‐tion de diverses méthodes de calcul théoriques montre que l'examen des charges frontières et le modèle à liaison délocalisée traduisctit le mieux les différences tie réuetivité constatées expéri‐mentalement.
Synthesis of some benzimidazole, benzoxazole and benzothiazole derivatives. Action of aliphatic selenonesters on some o‐phenylenediamine, o‐amino‐phenol and o‐aminothiophenol and their derivatives
Authors: Cohen Victor Israel , Pourabass Soraya 
Published: April 2009

AbstractAliphatic selenonesters react with o‐phenylenediamine, o‐aminophenol and o‐aminothiophenol and their derivatives to form benzimidazole, benzoxazole and benzothiazole derivatives, respectively. The mass and nmr spectra of the mentioned compounds were studied.
Cyclization of ylidenemalononitriles. X. Synthesis of benzazapropellane derivatives from α‐Cyano‐β‐chloroalkylcinnamonitriles
Authors: Campaigne E. , Mehra Ravindra K. 
Published: April 2009

AbstractThe reaction of nucleophilic and non‐nucleophilic bases wtih 2‐carbamoyl‐3‐(γ‐chloropropyl)‐1‐indenone (5) have been investigated. Condensation of γ‐chlorobutyrophenone with malono‐nitrile afforded α‐cyano‐β‐(3‐ehloropropyl)cinnamonitrile which was cyclized in concentrated sulfurie acid to produce 5. Two other products obtained from the cyclization reaction were 2‐carbamoyl‐3‐(γ‐ehloropropylidene)‐1‐indanone (4) and α‐carbamoyl‐β‐(3‐chloropropyl)cinnam‐amide.Treatment of a solution of 4 in ethyl acetate with piperidine resulted in cyclization of the γ‐chloropropyl side chain to give 2‐carbamoyl‐3‐cycIopropyl‐1‐indanone. The same compound was obtained in improved yield by the treatment of 4 or 5 with sodium hydroxide solution. The reaction of dirnethylamine with 5 in benzene gave initial Michael addition of the amine followed by internal alkylation of the carbanion so formed to yield 3a‐dimethylamino‐2,3,3a,8‐tetrahydro‐8‐oxoeyclopent[a]indene‐8a(lH)earboxamide (7a). Similarly addition of ammonia, pyrrolidine, piperidine, benzenethiol, p‐toluenethiol, 2‐naphthalenethiol and nitromethane to the indenone I gave respective analogs of type 7.Treatment of 5 with sodium cyanide in aqueous t‐butyl alcohol resulted in a similar Michael addition followed by internal alkylation. In addition, cyclization between the nitrile and the carbamoyl functions occurred in the same step to give 2‐oxo‐4‐imino‐7,8‐benzo‐3‐aza[3.3.3]‐propellan‐6‐one (13a). Hydrolysis of the iminopyrrolido ring in 13a to the corresponding suecin‐irnide gave 2,4‐dioxo‐7,8‐benzo‐3‐aza[3.3.3]propellan‐6‐one (13b). Reactión of 13b with methyl iodide, allyl bromide, benzyl bromide, and diethyluminoethyl chloride afforded the corresponding N‐alkylated products. A similar sequence starling with δ‐ehlorovalerophenone led to 5,6‐fused ring systems, including a [4.3.3]propellane. 2,9‐Dioxo‐4‐methyl‐7,8‐benzo‐3‐aza[4.3.3]propell‐4‐ene was obtained by the reaction of 5 with acetone in dilute alkali.
Condensation of ethyl phenylpropiolate with some cyanoacetyl and cyanomethylene heterocycles
Authors: Al‐Jallo Hikmat N. , Al‐Biaty Ibtisam A. , Al‐Azawi Fatin N. 
Published: April 2009

AbstractN‐Cyanoacetyl pyrrolidine, piperidine and morpholine reacted with ethyl phenylpropiolate to give the rearranged Michael addition products III. Some interesting results obtained from the bromination, hydrolysis and reduction of III are reported. 2‐Thiophene and 2‐furaneaceto‐nitriles reacted with ethyl phenylpropiolate to give the Claisen addition products XVIII. Reaction of either III or XVIII with hydrazine hydrate, phenylhydrazine and hydroxylamine hydrochloride afforded 3‐phenylpyrazol‐5‐one, 1,3‐diphenylpyrazol‐5‐one and 3‐phenylisoxazol‐5‐one together with the appropriate starting cyanoacetyl or cyanomethylene compounds, respectively. The mechanism for the formation of the various reaction products beside the ir and nmr spectral results are discussed.
Substituted 2,3‐dihydro‐4(1H)quinazoIinones, 2
Authors: Yale Harry L. 
Published: April 2009

AbstractDetails are given for the reaction of isatoic anhydrides with different primary aromatic amines to give several new N‐aryl‐o‐aminobenzamides. The latter were annulated with a variety of dialkyl and alkyl aryl ketones to give 2,3‐dihydro‐4(1H)quinazolinones. Several novel and efficient procedures for effecting the cyclization are described.
Synthetische untersuchungen zum reaktionsverhalten von 2‐phenyl‐5‐oxo‐5H‐naphtho[1,8‐bc] thiophen — thia‐pseudophenalenon
Authors: Neidlein R. , Kraemer A. D. 
Published: April 2009

AbstractThe reactivity of 2‐phenyl‐5‐oxo‐5H‐naphtho[1,8‐bc]thiophene (1) with the N‐sulfonyl‐heterokumulenes (2a‐2c, 2d‐2e. 2f‐2k) was of interest. We obtained the N‐sulfonylimino‐pseudophenalenones (5a‐5k). Phenylisocyanate and m‐chlorophenylisocyanate reacted with 1 only in the presence of the Lewis acid anhydrous aluminum chloride to give the derivatives 6a and 6b. From diphenylketene (7) and 1 we obtained the pseudophenafulvene 8, and from the fluorenketene (9) and 1 we obtained the pentapseudophenafulvalene 10.
Reaktionsverhalten von 2‐brom‐thiapseudophenalenon und 2‐brom‐thia‐pseudophenaleniumtetrafluoroborat
Authors: Neidlein R. , Seel H. 
Published: April 2009

AbstractThe reactivity of the 2‐bromothiapseudophenalenone (1) 2‐bromo‐5H‐naphtho[1,8‐bc]‐thiophen‐5‐one and of the 2‐bromothiapseudophenalenium salt (2) 2‐bromo‐5‐ethoxynaphtho‐[1,8‐bc]thiolium‐tetrafluoroborate towards the N‐nucleophilic compounds R‐NH2 (3) or R‐NH‐NH2 and the C‐nucleophilic molecules e.g., malonodinitrile, barbituric acid was of interest. We obtained the substituted hydroxyiminothiapseudophenalenone derivatives 4a‐g, 6a‐g, 7, 8, 9, 11a‐o, 12 and 14.