bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of 1‐alkyl‐2‐nitroimidazole‐5‐carboxaldehydes
Authors: Cavalleri Bruno , Ballotta Roberto , Lancini Gian Carlo 
Published: March 2009

AbstractWe report the preparation of 1‐methyl‐ and 1‐ethyl‐2‐nitroimidazole‐5‐carboxaldehydes (Ia,b). For Ia three different routes of synthesis are described, which appear of general value for preparing 1‐alkyl substituted 2‐nitroimidazole‐5‐carboxaldehydes.
Crystal and molecular structure of triphenyl 4,4,6‐Trimetliyl‐1‐oxa‐3‐azaeyeiohex‐2‐enylcarbenyl phosphonium chloride
Authors: Trefonas L. M. , Brown J. N. 
Published: March 2009

AbstractThe structure of the title compound has been determined by a single crystal, x‐ray diffraction study. The compound crystallizes in a monoclinic unit cell of P21/c symmetry and dimensions, a = 9.832 ± .001 Å, b = 15.398 ± .001 Å, c = 19.762 ± .002 Å, and β= 123.06 ± .01 ° with four molecules per unit cell. The 1633 statistically significant reflections (from a total of 2743 out to 20 = 100°) refined to a final value of R = 0.053. The molecule itself consists of a chloride ionically bonded to a cation containing a tetrahedral phosphorus bound to three phenyl rings and a fourth oxazine ring. It is the latter ring which displays extensive derealization as discussed in the paper.
Triazine chemistry VIII. 2,5‐dihydro‐5‐oxo‐1,2,4‐triazines
Authors: Lee Jaekeun , Paudler William W. 
Published: March 2009

Abstract2,5‐Dihydro‐5‐oxo‐1,2,4‐triazine and some of its alkylated derivatives have been prepared. Nmr spectroscopic analysis has established that the 2,5‐dihydro‐5‐oxo tautomers are preferred over the 4,5‐dihydro‐5‐oxo ones. This preference, and the behavior of 1,2,4‐triazines in some other chemical reactions has been interpreted in terms of electron‐electron repulsions between the lone pairs of electrons of N1 and N2 in this ring system.
Reactions of dichloromaleimides with alcohols, phenols, and thiols
Authors: Lynch D. M. , Crovetti A. J. 
Published: March 2009

AbstractThiols react with dichloromaleimides in the presence of base to give 2,3‐bis[alkyl(aryl)‐mercapto]maleimides. Alcohols and phenols in equivalent amounts give 2‐alkyl(aryl)oxy‐3‐chloromaleimides. With two equivalents, phenols give 2,3‐bis(aryloxy)maleimides, but alcohols give 2‐chloro‐3,3‐dialkoxysuccinimides in protic solvents and dimeric compounds in aprotic solvents.
Picrylamino‐substituted heterocycles. V. pyridines
Authors: Coburn Michael D. , Singleton Jannie L. 
Published: March 2009

AbstractThe condensation of various aminopyridines with picryl chloride and picryl fluoride has been investigated as part of our continuing effort in the field of picrylamino‐substituted heterocycles. In addition to the expected picrylamino derivatives we obtained the 1‐picryl derivatives of the imino forms of some of the amines.
Cyclic adrenaline derivatives. Aryl‐2‐Piperidyl‐Carbinols
Authors: Sankey G. H. , Whiting K. D. E. 
Published: March 2009

AbstractA synthetic route; to 3,4‐dihydroxyphenyl‐(2‐piperidyl)earbinols is described. These novel catecholamines may be regarded as derivatives of adrenaline containing a cyclic side‐chain moiety. Their biological action appears to be more selective than that of adrenaline or isoprenaline and the more active of these compounds show promise as powerful bronchodilators with minimum cardiac effect.
Studies on the syntheses of analgesics. Part XXXI. Synthesis of 1,2,3,4,5,6‐Hexahydro‐3‐methyl‐6‐phenyl‐2,6‐melhano‐2,3‐benzo[g] diazocine [studies on the syntheses of heterocyclic compounds. Part CDLXXIX]
Authors: Kamelani Tetsuji , Kigasawa Kazuo , Hiiragi Mineharu , Aoyama Toyohiko 
Published: March 2009

Abstract1,2,3,4,5,6 Hexahydro‐8‐methoxy‐3‐methyl‐6‐phenyl‐2,6‐methano‐2,3‐benzo[g]diazocine (IIa) was synthesized from 1‐(3‐methoxyphenyl)phenylaeetonitrile (III), readily available by the benzyne reaction of o‐chloroanisole with phenylacetonitrile, through several steps. Treatment of IIa with 47% hydrobromic acid afforded 1,2,3,4,5,6‐hexahydro‐8‐hydroxy‐3‐methyl‐6‐phenyl‐2,6‐methano‐2,3‐benzo[g]diazocine (IIb).
Aminomereuration X ‐ Synthese D'hétérocyeliques monospiranniques par aminomereuration intramoléculaire
Authors: Hodjat H. , Lattes A. , Laval J. P. , Périé J. J. , Moulines J. 
Published: March 2009

AbstractDans Ie cours général de recherches relatives à l'hétéroeyelisation de systèmes éthyléniques par aminomercuration, nous développons ici un exemple d'extension de cette réaction: la formation d'hétérocycles monospiranniques.
Reactions of Ketones XVI. 5,5‐I)imethoxy‐Δ2‐1,2,3‐triazoline/2,2‐Dimethoxy‐2‐aminodiazoethane Mutual Conversion
Authors: Scarpati R. , Craziano M. L. 
Published: March 2009

AbstractPhenylketene dimethylacetal reacts with ethyl azidoformate to give 1‐ethoxyearbonyl‐4‐phenyl‐5,5‐dimethoxy‐Δ2‐1,2,3‐triazoline (III). The behaviour of the latter and of its isomerization product, 1‐phenyl‐2,2‐dimethoxy‐2 (N‐ethoxyearbonylamino)diazoethane (IV), have been investigated in detail. The results point out a triazoline III/diazoethane IV mutual conversion.
PMR analysis of nitroquinoline 1‐Oxides
Authors: Roe Robert , Paul J. S. , Montgomery P.O'B. 
Published: March 2009

AbstractChemical shifts and coupling values obtained from the 100 MHz pmr spectra of 12 nitrosubstituted quinoline 1‐oxide derivatives are presented. Spin‐spin decoupling, application of the paramagnetic shift reagent tris‐(1,1,1,2,2,3,3‐heptafluoro‐7,7‐dimethyl‐4,6‐octanedione) europium (III), and calculations of theoretical spectra were used in matching signals to protons in the complex portions of the pmr spectra. Precise spectral parameters were obtained by application of an iterative technique provided by a published computer program. The identification of 4‐ and 5‐nitro substituted quinoline 1‐oxides by correlation of pmr spectral parameters with chemical structure is illustrated. The preparation and structural elucidation of two potential carcinogenic compounds, 2,6‐dimethyl‐4‐nitroquinoline 1‐oxide and 2,7‐dimethyl‐4‐nitroquinoline 1‐oxide are described.
Inhibitors of platelet aggregation. 4. [1,2,5]Thiadiazolo[3,4‐c]acridines, 7,8,9,10‐Tetrahydro[1,2,5] thiadiazolo[3,4‐c]acridities, and 8,9‐Dihydro‐7H‐cyclopenta[b][1,2,5] thiadiazolo[3,4‐H]quinolines
Authors: Elslager Edward F. , Haley Neil F. 
Published: March 2009

AbstractThe condensation of 4‐amino‐2,1,3‐benzothiadiazole (IV) with diphenyliodonium‐2‐earboxylate gave N‐(2,1,3‐benzothiadiazoI‐4‐yl)anthranilic acid (V) (28%), which was cyclized with phosphorus oxychloride to 6‐chloro[1,2,5]thiadiazolo[3,4‐c]acridine (VI) (84%). Treatment of VI with 3‐(dimethylamino)‐1‐propanethiol hydrochloride in phenol afforded 6‐[ [3‐(dimethylamino)‐propyl]thio] [1,2,5]thiadiazolo[3,4‐c]acridine (VII) (65%). The reaction of IV with a mixture of methyl and ethyl 2‐oxocyclohexanecarboxylate gave the adduct, which was ring closed in Dowtherm to 7,9,10,1 1‐tetrahydro[1,2,5] thiadiazolo[3,4‐c]acridin‐6(8H)one (VIII) (70%). Chlorination of VIII with phosphorus oxychloride gave 6‐chloro‐7,8,9,10‐tetrahydro[1,2,5]thiadiazolo[3,4‐c]acridine (IX) (84%), which was condensed with 3‐(dimethylamino)‐1‐propanethiol hydrochloride in phenol yielding 6‐[ [3‐(dimethylamino)propyl]thio]‐7,8,9,10‐tetrahydrof 1,2,5]‐thiadiazolo[3,4‐c]acridine (X) (27%). 6‐[ [3(1)imethylamino)propyl]thio]‐8,9‐dihydro‐7H‐cyclopenta[b] [1,2,5]thiadiazolo[3,4‐h]quinoline (XIII) (25%) was prepared similarly from IV and a mixture of methyl and ethyl 2‐oxocyclopentanecarboxylate via 7,8,9,10‐tetrahydro‐6H‐cyclopenta[b][1,2,5]thiadiazolo[3,4‐h]quinolin‐6‐one (XI) (85%) and 6‐chloro‐8,9‐dihydro‐7H‐cyclopenta[b][1,2,5]thiadiazolof3,4‐h]quinoline (XII) (56%). The effects of compounds VII‐XIII as inhibitors of platelet aggregation are discussed.
Folate antagonists. 7. Antimalarial, antibacterial, and antimetabolite effects of 2,4‐Diamino‐6‐(benzyl and pyridylmethyl)‐5,6,7,8‐tetrahydropyrido[4,3‐d] pyrimidines
Authors: Elslager Edward F. , Clarke Jane , Jacob Patricia , Werbel Leslie M. , Willis J. D. 
Published: March 2009

Abstract2 Various4‐diamino‐6‐(benzyl and pyridyhnethyl)‐5,6,7,8‐tetrahydropyrido(4,3‐d]pyrimidines (IX) have been synthesized for antimalarial and antibacterial evaluation. Alkylation of 4‐amino‐3‐cyano‐1,2,5,6‐tetrahydropyridine (VI) with the requisite α‐chlorotoluene or picolyl chloride in 2‐butanone afforded the corresponding 4‐amino‐3‐eyano‐1‐(benzyl and pyridvlmethyl)‐1,2,5,6‐tetraliydropyridines (VIII) (16–73%), which were cyclized to the pyrido[4,3‐d]pyrimidines (IX) utilizing guanidine carbonate in dimethylformamide. Alternatively, VI was condensed with guanidine carbonate in ethyl cellosolve to give 2,4‐diamino‐5,6,7,8‐tetrahydropyrido[4,3‐d]‐pyrimidine (VII) (52%), which upon treatment with the appropriate α‐ehlorotoluene in dimethyllormamide gave other 2,4‐diamino‐6‐benzyl‐5,6,7,8‐tetrahydropyrido[4,3‐d]pyrimidines (IX) (26–27%). Kight compounds were active orally against Plasmodium berghei in mice at doses ranging from 3.9 to 125 mg./kg./day for 6 days (0.6 to 19 times as potent as quinine hydrochloride), while three compounds displayed activity when administered in a single subcutaneous dose of 640 mg./kg. Four substances exhibited in vitro activity against Streptococcus faecalis (MGH‐2), normal (UC‐76) and drug‐resistant (S18713) Staphylococcus aureus, and Streptococcus pyogenes ((1203), with MIC's ranging from > 0.25 to 10 μg./ml. Data on the inhibitory effects of various pyrido[4,3‐d]pyrimidines against Streptococcus faecalis R (S. faecium var. durans, ATCC 8043), S. faecalis A (aminopterin, metholrexate‐resistant), and Lactobacillus plantarum (ATCC 8014) is summarized.
Quinazolincs. X. Direct formation of aminoquinazolines from hydroxyquinazolines and phenyl phosphorodiamidate
Authors: Rosowsky Andre , Papathanasopoulos Nickolas 
Published: March 2009

AbstractTreatment of several types of liydroxyquinazoline ring systems with phenyl phosphorodiamidate resulted in direct formation of the corresponding aminoquinazolines. The reaction can be conducted either by fusion in the absence of solvent or with diphenyl ether added as a diluent. The main advantage of the method is that it obviates the usual requirement for chlori‐nation or thiation prior to animation.
Quinazolines. XI. Synthesis of 2,4‐diamino‐5, 10‐diliydrobenzo[g] quinazolines
Authors: Rosowsky Andre , Burrows Elizabeth P. , Huang Ping C. , Modest Edward J. 
Published: March 2009

AbstractAn unequivocal synthesis of 2,4‐diamino‐5,10‐dihydrobenzo[g]quinazolines is described, starting from methyl 2‐tetralone‐3‐carboxylates. Condensation with guanidine yielded 2‐amino‐4‐hydroxy derivatives, which were thiated with phosphorus pentasulfide and S‐alkylated with dimethyl sulfate. The resultant 2‐amino‐4‐methylthio compounds were converted into 2,4‐diamino derivatives by amination at elevated temperature and pressure. Attempted synthesis from 3‐cyano‐1,4‐dihydro‐2‐methoxynaphthalene and guanidine was unsuccessful.
Novel polycyclic heterocycles. X. Synthesis of 3‐amino derivatives derived from 1,2‐dihydro‐l 1 (trifluoromethyl)‐3H,7H‐quino [8,1‐cd][ 1,5]benzoxazepin‐3‐one
Authors: Petigara Ramesh B. , Yale Harry L. 
Published: March 2009

AbstractThe reactions of the tetracyclic ketone, 1,2‐dihydro‐11‐(trifluoromethyl)‐3H,7H‐quino[8,1‐cd] [1,5]benzoxazepin‐3‐one (1) with pyrrolidine, piperazine, N‐methylpiperazine, and dimethyl‐amine gave the enamines 2, 13, 11, and 4. These were reduced with sodium borohydride to the corresponding 3‐amino derivatives 3, 14, 12, and 5. The 3‐(2‐hydroxyethylpiperazino) derivative (8) was obtained from the 3‐chloro compound (7); 7 was prepared from the carbinol (6). The 3‐NH2 derivative (10) was obtained by reduction of the oxime (9). In 3, 5, 6, 7, 8, 10, 12, and 14, the ‐OCH2 protons were non‐equivalent, since in the pmr spectrum of each of these compounds there was seen a symmetrical, perturbed AB quartet, with a common JAB of 12 cps, that must be attributed to geminal interproton coupling. This phenomenon had not previously been observed with 1, 9, or the enamines, since in their pmr spectra, the ‐OCH2 protons had invariably been seen as singlets.
The synthesis of pseudorutaecarpine with triethyl phosphite
Authors: Kametani Tetsuji , Yamanaka Tohru , Nyu Kiyosato 
Published: March 2009

AbstractPseudorutaecarpine was synthesized by nitrene reaction of 3‐(2‐nitrobenzal)‐1,2,3,9‐tetra‐liydropyrrolo[2,1‐b]quinazolin‐9‐one (IV).
Acid‐catalyzed rearrangement of 2‐phenyl‐2,3‐dihydro‐1,4‐benzoxazepin‐5(4H)ones
Authors: Misiti D. , Rimatori V. 
Published: March 2009

Abstract2‐Phenyl‐2,3‐dihydro‐1,4‐benzoxazepin‐5(4H)ones (I) were converted into 2‐(o‐hydroxyaryl)‐5‐plienyl‐2‐oxazolines (II) and 3,4‐diliydro‐4‐plienyl‐8‐hydroxyisoearbostyrils (III) by concentrated sulfuric acid. The ratio of II and III is dependent upon substituents present in the aromatic ring of the parent benzoxazepinones.
Photo‐decarbonylation of β‐styryl isocyanates
Authors: Boyer J. H. , Mikol G. J. 
Published: March 2009

Abstractβ‐Styryl isocyanate (1, R  H) and its β‐methyl‐ (1, R  CH3) and β‐phenyl‐ (1, R  C6H5) derivatives underwent both extensive polymerization and the loss of the elements of carbon monoxide upon irradiation at 254 nm in cyclohexane. The formation of 2,5‐diphenylpyrazine (3) and indole 4, (R  H) from 1, (R ‐ H) and 2,3‐dimethyl‐5,6‐diphenylpyrazine (6) and 2‐methylindole (4, R  CH3) from 1, (R  CH3) provided diagnostic evidence for styryl nitrene (2a) intermediates. The formation of both phenylacetonitrile (5, R  H) and α‐phenylpropio‐nitrile (5, R  CH3) was assigned to an initial rearrangement of the residue, C8H6(R)N̈: (2), into a ketenimine concerted with the elimination of carbon monoxide from 1. Isomerization then produced a nitrile. β3‐(β‐phenyl)styryl isocyanate (1, R  C6H5) gave no product requiring the intermediacy of a nitrene and/or an azirine. The formation of 2,3,4,5‐tetraphenylpyrrole (8) was assigned to a dimerization of the isocyanate concerted with or following the elimination of the elements of carbon monoxide and isocyanic acid, and the formation of 3‐phenylisocarbo‐styril (9) was assigned to a ring‐closure of the isocyanate in an excited triplet state. Each isocyanate gave stilbene and trace amounts of oxidative fragmentation into benzaldehyde and benzonitrile. Solvent participation produced benzylcyclohexane and bicyclohexyl. Two unidentified solids, C17H14N2O and C12H14N2O, were obtained from 1, (R  CH3).
The chlorinalion of 3,5‐dimethyl‐1,2,4‐oxadiazole
Authors: Burden John A. , Heywood Donald L. 
Published: March 2009

AbstractThe clilorination of 3,5‐dimethyl‐1,2,4‐oxadiazole has been studied using both photo and thermal initiation. It has been found that photoinitiation allows reaction at both the 3‐ and 5‐methyl group, the former being preferred by a factor of 3‐4 at moderate (up to 75° ) temperature. The difference in reactivity is related to a difference in electron availability at the two reaction sites. The thermally initiated chlorination occurs almost exclusively at the 5‐methyl group. Overall, 3,5‐dimethyl oxadiazole is much less active than toluene or cyclo‐liexane toward chlorination.
Reaction of sulfene with heterocyclic α‐dialkylaminomethyleneketones II. Synthesis of 5N‐1,2‐oxathiino[5,6‐c] [1]benzopyran derivatives
Authors: Schenone P. , Morasso S. , Bignardi G. 
Published: March 2009

AbstractThe reaction of sulfene with 3‐dialkylaminomethylene‐4‐chromanone and 3‐dialkylamino‐methylene‐6‐methyl‐4‐ehromanone gave 1,4‐cycloadducts which are derivatives of a new heterocyclic system, i.e., 5H‐1,2‐oxathiino[5,6‐c][1]benzopyran. The structures of the adductswere determined by ir and nmr spectral data. Two new α‐hydroxymethyleneketones (3‐hydroxy‐methylene‐4‐chromanone and its 6‐methyl analogue) as well as some of their derived enamines were prepared. During the preparation of N,N‐diethylenamines a self‐condensation occurs, which gives the byproducts Xa‐b.
Ring closure reaction of 4‐(2‐hydroxyanilino)‐2‐phenyl‐5‐pyrimidinecarboxylic acid with acetic anhydride. Synthesis of pyrimido[5,4‐c] [1,5]benzoxazepin‐5(11H)ones
Authors: Kim Dong Han , Santilli Arthur A. , Fieber Richard A. 
Published: March 2009

AbstractSyntheses of 11‐acety1‐2‐phenylpyrimido[5,4‐c][1,5]benzoxazepin‐5(11H)one (16a) and analogs (16b,c, 22) were described. The reaction of 4‐chloro‐2‐phenyl‐5‐pyrimidinecarboxylic acid ethyl ester (7) with 2‐aminophenol afforded 4‐(2‐hydroxyanilino)‐2‐phenyl‐5‐pyrimidine‐carboxylic acid ethyl ester (8a). The latter was also prepared by catalytic reduction of 4‐(2‐nitrophenoxy)‐2‐phenyl‐5‐pyrimidinecarboxylic acid ethyl ester (9), which was obtained from 7 and 2‐nitrophenol. Involvement of 4‐(2‐aminophenoxy)‐2‐phenyl‐5‐pyrimidinecarboxylic acid ethyl ester (12a) in this reduction as an intermediate was demonstrated by an independent synthesis of 12a and its subsequent rearrangement to 8a. Hydrolysis of 8a or 12a gave 4‐(2‐hydroxyanilino)‐2‐phenyl‐5‐pyrimidinecarboxylic acid (15a). Reaction of 15a with acetic anhydride afforded 16a, the first member of a novel ring system, the pyrimido[5,4‐c][1,5]‐benzoxazepin. Additional examples (16b,c) were prepared similarly. The corresponding 11‐ethyl derivative (22) was prepared in similar fashion, starting with 7 and 2‐ethylaminophenol. A possible reaction mechanism for the formation of 16a‐c from 15a‐c and acetic anhydride was discussed.
Halogenation of pyridine 1‐oxides
Authors: Abramovitch R. A. , Campbell J. , Knaus E. E. , Silhankova A. 
Published: March 2009

AbstractThe chlorination and bromination of α‐lithiopyridine 1‐oxides has been studied. Only dihalogenated pyridine 1‐oxides are formed. In the case of bromination dipyridyl derivatives are also formed, and, indeed, predominate. Chloromercuration of the lithiopyridine 1‐oxides gave highly insoluble, unresolvable mixtures of pyridylmercury derivatives. These could be brominated readily to give mixtures of 2‐bromo‐ and 2,6‐dibromopyridine 1‐oxides.
Maerocyelic polyether sulfide syntheses. The preparation of thia‐crown‐3,4, and 5 compounds
Authors: Bradshaw J. S. , Hui J. Y. , Haymore B. L. , Christensen J. J. , Izatt R. M. 
Published: March 2009

AbstractMacrocyelic polyether sulfides have been prepared by reacting an oligoethylene glycol dichloride with a dithiol or sodium sulfide in ethanol. The trivial naming system for these compounds is an extension of the trivial crown nomenclature (5). A thia prefix is used to show that sulfur atoms have replaced ether oxygen atoms in the polyether ring. The following new compounds were prepared: 1‐thia‐(15‐crown‐5) (II) 1,4‐dithia‐(15‐crown‐5) (III) 1,7‐dithia‐(15‐crown‐5) (IV) 1,4‐dithia‐(12‐crown‐4) (VII) 1,4,7‐trithia‐(12‐crown‐4) (VIII) 1‐thia‐(9‐crown‐3) (IX) and 1,4‐dithia‐(9‐crown‐3) (X). Four other previously reported maerocyelic polyether sulfides were also prepared. The symmetry of the nmr spectra of these compounds gives added evidence for the proposed ring structures.
Azole chemistry. V. Synthesis and spectral properties of thiazolo[3,2‐d] tetrazolium salts
Authors: Alper Howard , Stout Richard W. 
Published: March 2009

AbstractThiazolo[3,2‐d] tetrazolium salts were obtained by treatment of 5‐mercapto‐1‐phenyl‐1,2,3,4‐tetrazole with α‐bromo ketones followed by cyclodehydration. The spectral properties of the salts and the β‐keto sulfide precursors were investigated.
Synthesis of pyrazoles and oxyquinoxalines from 2,4‐dioxohexenoales
Authors: El Khadem H. , El‐Shafei Zaki , Rateb Latif , Mokhtar Hassan 
Published: March 2009

AbstractCondensation of ethyl 2,4‐dioxo‐6‐phenylhex‐5‐enoates (I; R = H, I; R = Me, I, R = Ph) with various hydrazines yielded ethyl 5‐styrylpyrazole‐3‐carboxylates (III), which were hydrolyzed to the acids (IV), and ozonized to 5‐keto pyrazole esters (VI) and acids (VII). Reduction of the 5‐formylpyrazoles (VI; R = II) with borohydride afforded the 5‐hydroxymethyl derivatives (VIII). The same 2,4‐dioxohexenoates (I) when treated with o‐phenylenediamine gave 2‐oxy‐quinoxalines (V; R = H, V; R = Me, V; R = Ph). The uv spectra data of these compounds are given.
Studies on the syntheses of heteroeyelie compounds. Part DV. Cyclization products of i‐substituted 2‐benzyl‐1,2,5,6‐tetrahydropyridines [syntheses of analgesics. Part XXXV]
Authors: Kametani Tetsuji , Kigasawa Kazuo , Hiiragi Mineharu , Wagatsuma Nagatoshi , Uryu Tuneo , Sugi Hideo 
Published: March 2009

AbstractTreatment of 1,2,5,6‐tetrahydro‐2‐(4‐hydroxy‐ and/or 4‐methoxybenzyl)‐3,4‐dimethyl‐I‐(3‐methyl‐2‐butenyl)pyridines (IV and V) and 2‐(4‐methoxybenzyl)‐3,4‐dimethyl‐1‐(3‐methyl‐2‐butenyl)‐4‐piperidinol (X) with acid afforded 9‐(4‐hydroxy‐ and/or 4‐methoxybenzyl)‐4,4,5,6‐tetramethyl‐1‐azabicyelo[3,3,1]non‐6‐ene (XIII and XIV). In contrast, the corresponding 1‐allyl‐substituted derivatives VI, VII, and XI were converted into the expected 3‐allyl‐1,2,3,4,5,6‐hexahydro‐8‐hydroxy‐ and/or 8‐methoxy‐6,11‐dimethyl‐2,6‐methano‐3‐benzazocine (II and III).
Studies on the syntheses of heteroeyelie compounds. Part DVII. A synthesis of (±)‐N‐norgalanthamine
Authors: Kametani Tetsuji , Yamaki Kazuya , Terui Tsunekazu 
Published: March 2009

Abstract(±)‐N‐Norgalanthamine (la) and (±)‐N‐norlycoramine (Ib) was synthesized through the phenolie oxidation of N‐(4‐hydroxyphenethyl)‐2‐bromo‐5‐hydroxy‐4‐methoxybenzamide (lIb).
Intramolecular nucleophilic cyclization of 3‐substituted pyridylalkylamines onto the 2‐position of the pyridine ring
Authors: Hawes Edward M. , Davis Hubert Lome 
Published: March 2009

AbstractThe intramolecular nucleophilic cyclization of 4‐(3‐pyridyl)butylamine (4a) to yield 6,7,8,9‐tetrahydro‐5H‐pyrido[2,3‐b]azepine (5) was investigated. Of eleven different alkali metal reagents sodium, sodium hydride, sodium amide, and potassium hydride gave good yields of 5. The sodium conditions when applied to 3‐(3‐pyridyl)propylamine (4b) afforded 1,2,3,4‐tetrahydro‐1,8‐naphthyridine (6) in good yield.
Silver and palladium complexes of some aromatic azo and azoxy compounds
Authors: Porter John J. , Murray Joel Luke , Takvorian Kenneth B. 
Published: March 2009

AbstractThe complexing ability of derivatives of azobenzene (I) is well known (I) and responsible for the production of a wide variety of dyestuffs and analytical chemicals. While the azo group generally participates in the coordination, the determination of the degree of its interaction is complicated by other functional groups which are also coordinated with the transition metal. In a previous publication (2), we reported the preparation of the silver and palladium complexes of benzo[c]cinnoline (II) and proposed that these results might be used to explain the electron donor properties of azobenzene. We are now reporting the preparation of some additional complexes with ligands containing the azo group.
Synthesis of 2,2′‐bipyrimidine derivatives
Authors: Feit B. A. , Teuerslein A. 
Published: March 2009

AbstractA new total synthesis of 2,2′ ‐bipyrimidine derivatives by the direct condensation of 2‐amidinopyrimidinebenzenesulfonate with dicarbonyl compounds is described. The following 2,2′‐bipyrimidines have been prepared: 5‐ethyl‐4,6‐dihydroxy‐2,2′‐bipyrimidine; 5‐ethyl‐4,6‐dichloro‐2,2 ‐bipyrimidine; 4,6‐dihydroxy‐2,2′ ‐bipyrimidine; 5‐ethyl‐4,6‐dimethoxy‐2,2′ ‐bipyrimidine.
Studies on the hydrolysis of cyclophosphamide II. Isolation and characterization of intermediate hydrolytic products
Authors: Chakrabarli Jiban K. , Friedman Orrie M. 
Published: March 2009

AbstractTwo new products of hydrolysis of cyclophosphamide in water at 100°,N‐(2‐chloroethyl)‐N' ‐(3‐phosphatopropy l)ethylenediamine andN‐(2‐hydroxyethyl)‐N‐(3‐phosphatopropyl)ethylene‐diamine, have been isolated after 30 minutes, and 6 hours of reaction times, respectively. These products have been shown to be intermediates leading to the formation ofN‐(2‐hydroxyethyl)‐N'‐(3‐hydroxypropyl)ethylenediamine, the principal ultimate product of cyclophosphamide hydrolysis. The nature of these new products supports the previously postulated mechanism involving an intramolecular alkylation as the initial step in the hydrolytic process although the pathway appears to be an unlikely model for the metabolic transformations of cyclophosphamidein vivo.