bluuebunny/crossref_metadata_2025_split huggingface dataset:
An improved general synthesis of 4‐aryl‐5‐pyrimidinecarboxylates
Authors: Breaux Eves J. , Zwikelmaier Kurt E. 
Published: March 2009

AbstractWe wish to report an improved, general synthesis of 4‐aryl‐5‐pyrimidinecarboxylates 1. Two different routes have previously been reported for the synthesis of examples of this class of pyrimidine carboxylates. The parent compound, ethyl 4‐phenyl‐5‐pyrimidinecarboxylate was prepared in low yield by the reaction of s‐triazine with ethyl benzoyl acetate. In addition, the enol ether β‐ketoaldehyde synthon, ethyl 2‐benzoyl‐3‐ethoxy‐2‐propenoate, was reported to give 1a in modest yield when reacted with guanidine (2).
The electron impact fragmentation of 3‐ and 4‐styrylpyridazine
Authors: Heresch Franz , Allmaier Guenter , Heinisch Gottfried 
Published: March 2009

AbstractThe electron impact mass spectrometric fragmentation of trans‐3‐ and trans‐4‐styrylpyridazine is reported in detail, including a comparison with other aza‐stilbenes. With regard to a distinction between the two isomeric styrylpyridazines, the intensity ratio of the M+ and [M‐1]+ ions, the general degree of fragmentation and the elimination pathways of nitrogen proved to be most characteristic.
Synthesis of 1‐methyl‐ and 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines as potential anticonvulsant agents
Authors: Kornet Milton J. , Chu John 
Published: March 2009

Abstract1‐Methyl‐ and 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines were synthesized and examined for anticonvulsant activity in the maximal electroshock seizure and pentylenetetrazol seizure threshold tests. One synthetic pathway for the 1‐methyl compounds involved the reaction between aryl isocyanates and 1‐methyl‐piperidazine. A second procedure, of lesser utility, utilized selective lithium aluminum hydride reduction of 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines and gave the corresponding 1‐methyl compounds. The 1‐ethoxycarbonyl series was obtained from aryl isocyanates and 1‐ethoxycarbonylpiperidazine. Several 1‐methyl‐2‐phenylcarbamoylpiperidazines exhibited significant anticonvulsant activity.
Studies on the synthesis of heterocyclic compounds. Part V. A novel synthesis of some pyridazin‐4‐(1H)one derivatives and their reaction with hydrazine
Authors: Plescia Salvatore , Daidone Giuseppe , Fabra Jole , Sprio Vincenzo 
Published: March 2009

AbstractSome phenylazo derivatives of β‐dicarbonyl compounds 1a,b,c,d reacted with dimethylformamide dimethylacetal to yield new 1‐phenyl‐3‐R‐4‐(1H)pyridazinones 3a,e and 4. When compounds 3a and 3e were treated with hydrazine hydrate, they gave rise to pyrazolo[4,3‐c]pyridazines 5 and 7, respectively. By the action of hydrazine hydrate on compound 4, the 1‐phenyl‐3‐(1H‐pyrazol‐3‐yl)‐4‐(1H)pyridazinone 8 was obtained. The structures of all the new compounds were assigned on the basis of satisfactory analytical and spectroscopic data.
Reactions of 3‐acetyltropolone methyl ethers with o‐phenylenediamine. Formation of cyclohepta[b][1,5]benzodiazepine
Authors: Imafuku Kimiaki , Yamane Akio , Matsumura Hisashi 
Published: March 2009

AbstractReactions of 3‐acetyltropolone methyl ethers with o‐phenylenediamine are described. 3‐Acetyl‐2‐methoxytropone (2a) with o‐phenylenediamine in ethanol under reflux condition to afford 11‐hydroxy‐6‐methylcyclohepta[b][1,5]benzodiazepine (4), 10‐acetyl‐6H‐cyclohepta[b]quinoxaline (5), and 6‐acetyl‐5H‐cyclohepta[b]‐quinoxaline (6). The same reaction of 7‐acetyl‐2‐methoxytropone (2b) gave 7‐acetyl‐2‐(2‐aminoanilino)‐tropone (3b) besides 4, 5, and 6. The compound 4 has a 1,4‐diazaheptalene skeleton.
1‐Acetamido‐17‐carbomethoxydihydrothebainone
Authors: Archer Sydney , Okaniwa Kenichiro , Schepis Dominic J. , Moharir Yadunath E. , Klinowski Carl W. 
Published: March 2009

AbstractTreatment of 1‐(5′‐benzyloxy‐4′‐methoxy‐2′‐nitrobenzyl)‐3,4‐dihydroisoquinoline 2 with lithium/ammonia followed by the addition of ethanol gave a mixture of the dibenz[b,g]indolizines 3 and 4. Omission of ethanol resulted in the formation of 3 only. The dihydroisoquinoline from 3,4‐dimethoxyphenylethyl amine behaved similarly.Reduction of 2a with sodium/ammonia resulted in cleavage to give the nitro‐guaiacol 8. Oxidation of 2a in the presence of potassium t‐butoxide gave a complex mixture from which the benzoyldihydroisoquinoline 5 and 2‐benzyloxy‐5‐nitroanisole were isolated in low yield.Treatment of the hexahydrobenzylisoquinoline 10 with diazotized sulfanilic acid, followed by reduction and then acetylation gave a diacetyl compound 12 which was hydrolyzed to 13. Ring closure with boron trifluoride gave the dihydrothebainone 14.
Carbocyclic analogs of thymine nucleosides and related 1‐substituted thymines
Authors: Shealy Y. Fulmer , O'Dell C. Allen , Thorpe Martha C. 
Published: March 2009

AbstractThe carbocyclic analogs of thymidine (IXf), 1‐β‐ribofuranosylthymine (IXg), and 1‐β‐3′‐deoxyribofuranosyl‐thymine (IXe) were synthesized by incorporating modifications into the Shaw method of synthesizing 2,4‐(1H,3H)pyrimidinediones via acryloylureas. Simpler analogs of thymine nucleosides were also prepared by this method. The carbocyclic analog of thymidine displayed modest activity against Leukemia L1210 in vivo. It differs from a compound prepared previously by a Prins reaction.
Displacement of the indolyl sulfide linkage in the synthesis of 3‐substituted indoles
Authors: Bennett Richard , Maggiolo Allison , Shah Tushar 
Published: March 2009

AbstractThe indolyl sulfide compounds (5,6,7,8) gave 3‐3′‐diindole methane derivatives by a double decomposition‐displacement reaction. These same compounds when reacted with alkoxides yielded 3‐alkoxy‐methylindole derivatives (9‐14).
Heterocycles. 9. 2‐Aryl‐2H‐1,4‐tetrahydrooxazines
Authors: Meyer Donald R. , Weintraub Philip M. 
Published: March 2009

AbstractReaction of 2‐bromo‐1‐phenylethanones with diethanolamine gave 2‐hydroxymorpholines. Acetylation gave mono or diacetates. Acid catalyzed dehydrations gave several types of products whose structures are discussed.
The crystal structures of 10‐oxa‐1,4,7‐trithiacyclododecane, 7,10,13‐trioxa‐1,4‐dithiacyclopentadecane, 7,10,13,16‐tetraoxa‐1,4‐dithiacyclooctadecane and 4,7,13,16‐tetraoxa‐1,10‐dithiacyclooctadecane
Authors: Dalley N. Kent , Larson Steven B. , Smith Judith S. , Matheson K. Lee , Izatt Reed M. , Christensen James J. 
Published: March 2009

AbstractThe structures of four macrocyclic polyether sulfides have been determined by single crystal x‐ray diffraction methods. The compounds studied were 1,4,7‐trithia‐12‐crown‐4, 1,4‐dithia‐15‐crown‐5, 1,4‐dithia‐18‐crown‐6 and 1,10‐dithia‐18‐crown‐6. In all four compounds the potential donor sulfur atoms point out of the ring. This causes the rings to be irregularly shaped.
Synthesis of cis‐ and trans‐1,3‐dicarbomethoxy‐2‐aminoisoindoline
Authors: Sanaa Paolo , Savelli Francesco , Cignarella Giorgio 
Published: March 2009

AbstractThe title compounds (4a,b) were synthesized starting with dimethyl α,α'‐dibromo‐o‐benzenediacetate and t‐butyl carbazate. Alternate approaches to 4 involving reduction of the appropriate 2‐nitrosoisoindoline were found unsuitable because of predominant side reactions.
Chemistry of the phenoxathiins and isosterically related heterocycles. XVI. The synthesis and molecular structure of 3‐azaphenoxathiin: Evidence in support of factors responsible for control of the dihedral angle
Authors: Caldwell Steven R. , Martin Gary E. , Simonsen Stanley H. , Inners Ruth R. , Willcott M. Robert 
Published: March 2009

AbstractThe synthesis of the 3‐azaphenoxathiin ring system and its molecular structure are reported. Based on 13C‐nmr chemical shift additivities associated with the insertion of an annular nitrogen atom and the observed 13C‐nmr shift of Cα, the title compound was predicted to have a dihedral angle θ = 160.2°. The observed dihedral angle from the crystal structure was found to be θ = 167.07° which is in reasonably good agreement with the predicted value. It is proposed that the position of the annular nitrogen atom is solely in‐control of the observed dihedral angle.
Novel heterocycles. 7. Reaction of 2‐chloronicotinonitrile with thioureas. Synthesis of the pyrido[2,3‐d]pyrimido‐[2,1‐b][1,3]thiazine ring system
Authors: Coppola Gary M. , Shapiro Michael J. 
Published: March 2009

AbstractN,N'‐Dimethylthiourea and 3,4,5,6‐tetrahydro‐2‐pyrimidinethiol were allowed to react with 2‐chloro‐nicotinonitrile (1) and their products investigated by standard methods and by carbon‐13 nmr. In both instances, displacement of the chlorine occurred by nitrogen not the sulfur of the thioureas. Secondary cyclizations occurred by attack of nitrogen on the nitrile to furnish 3a, and by sulfur on the nitrile to give 4b, a new ring system. Tricyclic 4b was hydrolyzed in dilute acid to give 5, or alkylated with methyl iodide in the presence of sodium hydride to give the ring opened product 6.
Synthesis and antihypertensive properties of a novel series of 3‐substituted amino‐s‐triazolo[3,4‐α]phthalazine derivatives
Authors: Omar A.‐Mohsen M. E. , Kasem M. Gabr , Laabota I. M. , Bourdais J. 
Published: March 2009

AbstractA novel series of 3‐substituted amino‐s‐triazolo[3,4‐a]phthalazine derivatives has been synthesized by the one‐pot cyclodesulfurization reactions utilizing 1‐hydrazinophthalazine, alkyl, aryl, or aralkylisothiocyanates and dicyclohexylcarbodiimide (DCCD) mixtures. The products did not exhibit any antihypertensive properties. Their pmr and mass spectral analysis is given.
Reaction of 4‐chloro‐3‐nitrocoumarin with glycine and alanine, and the synthesis of 1‐benzopyrano[3,2‐c]pyrimidine‐3,5‐dione
Authors: Stunić Z. , Trkovnik M. , Laćan M. , Janković R. 
Published: March 2009

AbstractA considerable improvement of the yields obtained in substitution of halogens in 4‐chloro‐3‐nitrocoumarin by amino acid or amino acid ester residues was achieved over literature claims. Electrochemical reduction of the nitro group in these products brought about a ring closure leading to benzopyranopyrimidinones, which are obtained in excellent yields.
Synthesis of 4‐β‐D‐arabinofuranosyl‐5,6‐dihydro‐2H‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide and x‐ray diffraction analysis of its 2′,3‐anhydro precursor
Authors: Schroeder A. C. , Srikrishnan T. , Parthasarathy R. , Block A. 
Published: March 2009

AbstractReaction of 2‐amino‐3′,5′‐bis(O‐tert‐butyldimethylsilyl)‐β‐D‐arabinofuran[1′,2′:4,5]‐2‐oxazoline with 2‐chloroethylsulfonyl chloride in the presence of sodium bicarbonate followed by removal of the protecting groups gave 2′,3‐anhydro‐4‐β‐D‐arabinofuranosyl‐5,6‐dihydro‐2H‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide (5), which by treatment with ammonia was converted to 4‐β‐D‐arabinofuranosyl‐5,6‐dihydro‐2H‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide (6). The structure of compound 5 was unequivocally established by means of an x‐ray diffraction analysis. The compound crystallized in the space group P212121 with unit cell dimensions a = 5.883(3), b = 9.352(2), c = 18.769(7) Å, Z = 4. Its structure was established by direct multisolution techniques and refined by the full matrix least squares method to a final R value of 0.058 for the 1515 reflections observed.
Pyrimidinylalkylthiols, furo[2,3‐d]pyrimidines and derivatives
Authors: Furukawa Sunao , Takada Mitsutaka , Castle Raymond N. 
Published: March 2009

AbstractSeveral pyrimidinylalkylthiols and furo[2,3‐d]pyrimidines and their derivatives have been prepared as potential radiation‐protection agents.
Synthesis via pummerer intermediates. IV. Synthesis of 1‐(4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)pyridinium hydroxide inner salt derivatives and 3‐(2H)benzofuranones by the action of phosgene in pyridine on 2‐hydroxy‐1‐[(methylsulfinyl)acetyl]benzene derivatives
Authors: Connor David T. , Sorenson Roderick J. 
Published: March 2009

AbstractThe treatment of ketosulfoxide 1 with phosgene in pyridine gave a mixture of 1‐(4‐hydroxy‐8‐methoxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)pyridinium hydroxide inner salt (4) and 7‐methoxy‐2‐(methylthio)‐3‐(2H)benzofuranone (7). Ketosulfoxides 8 and 11 behaved similarly. The inner salt structure assigned to compounds 4, 10, and 13 was confirmed by the unambiguous synthesis of 10 and 13 from hydroxycoumarins 15 and 18.
The synthesis of pyridine derivatives from 3‐formylchromone
Authors: Haas Georges , Stanton James L. , Von Sprecher Andreas , Wenk Paul 
Published: March 2009

Abstract3‐Formylchromone (1) reacts with active methylene derivatives to yield condensation products2a‐d, 10,11and12. Treatment of2a‐dwith ammonia or methylamine gives pyridines3–6. Alternatively, reaction of1with enamine derivatives yields pyrido compounds15, 17, 19, 21, 23and28in one step. Factors determining the formation and regiospecificity of the pyridine ring forming reactions are also discussed.
Carboxylation and acylation of 4,7‐dimethoxyindoles and a study of the corresponding dealkylated derivatives
Authors: Malesani Giorgio , Chiarelotto Gianfranco , Ferlin Maria Grazia , Masiero Sergio 
Published: March 2009

AbstractTreatment of 4,7‐dimethoxyindoles 1 and 9 with ethylmagnesium bromide and ethyl chloroformate in refluxing dry ether gives the corresponding indole‐1‐carboxylic acid ethyl esters 3 and 10 as major products, together, with minor amounts of indole‐3‐carboxylic acid ethyl esters 2 and 11. Similar treatment of 4,7‐dimethoxyindole (1) with ethylmagnesium bromide and chloroacetyl chloride affords the related 3‐chloroacetyl derivative 13. All of the new 4,7‐dimethoxyindole compounds were dealkylated with anhydrous aluminium chloride in refluxing dry benzene. Transformation of these demethylated indoles into other interesting derivatives, in view of possible antimicrobial activity is also reported.
The synthesis of heteroaromatic nitro compounds from 3‐nitrochromone
Authors: Haas Georges , Stanton James L. , Winkler Tammo 
Published: March 2009

Abstract3‐Nitrochromone (1) reacts with a series of nucleophiles by Michael addition followed by intramolecular condensation to yield pyrrolyl (2), phenyl (3), pyridyl (4), pyrido (5,6), pyrimidyl (7) and pyrazolyl (8) nitro derivatives. The reactions proceed under basic catalysis in 39–78% yields. Conversion of 4 to 3,4‐dihydrobenzofuro[3,2‐b]quinol‐1‐(2H)one (12) is also described. Carbon‐13 data for 2, 5, 6 and 8 are discussed. The one bond C,H coupling constants in the nitropyridines are also reported and used as an analytical tool.
Anticonvulsant activity and succinate dehydrogenase inhibitory property of new substituted thiobarbiturates
Authors: Dhasmana Anjali , Barthwal J. P. , Pandey B. R. , Ali B. , Bhargava K. P. , Parmar S. S. 
Published: March 2009

AbstractEight 1‐aryl‐3‐(2‐pyridyl)thiobarbiturates were synthesized and evaluated for their anticonvulsant property and their ability to inhibit succinate dehydrogenase activity of rat brain homogenates. These substituted thiobarbiturates (100 mg./kg., i.p.) provided 20–60% protection against pentylenetetrazol‐induced convulsions in albino mice. Low toxicity of these compounds was reflected by their high approximate LD50values which were found to range from 500–1000 mg./kg. All substituted thiobarbiturates (ImM) inhibitedin vitrosuccinate dehydrogenase activity and the degree of inhibition ranged from 10–72%.
Synthesis of 3‐formyltetronic acid and enamine derivatives
Authors: Gelin Suzanne , Chantegrel Bernard 
Published: March 2009

AbstractThe first reported synthesis of 3‐formyltetronic acid and its conversion to enamine derivatives is described. 3‐Dimethylaminomethylene‐2,4‐dioxotetrahydrofuran derivatives were also prepared by treatment of tetronic acids with dimethylformamide diethyl acetal. Nmr spectral studies are included.
Tetronic acids and derivatives. Part XI . Structure of coupling products of tetronic acids with benzenediazonium sulfate
Authors: Gelin Suzanne , Pollet Patrick 
Published: March 2009

Abstract13C Nmr, 1H nmr and ir parameters of coupling products of tetronic acids (4‐hydroxy‐5H‐furan‐2‐ones) with benzene diazonium sulfate are only consistent with a phenylhydrazone formulation with an almost equal ratio of the syn and anti configurations. These results contrast with those of coupling products of acyclic 3‐ketoesters, existing mainly as anti tautomers, and more sharply with the 3‐parabromophenylhydrazone of L‐dehydro ascorbic acid, which is exclusively syn.
Mononuclear heterocyclic rearrangement. Part 6 . Studies on base catalysis of the rearrangement of the (Z)‐p‐nitrophenylhydrazone of 3‐benzoyl‐5‐phenyl‐1,2,4‐oxadiazole in benzene: Effect of piperidine, triethylamine and of some secondary amines
Authors: Frenna Vincenzo , Vivona NicolÒ , Spinelli Domenico , Consiglio Giovanni 
Published: March 2009

AbstractThe kinetics of the title reaction catalyzed by various secondary and tertiary amines have been measured at 40° in benzene. The catalysis laws which were observed confirm the previous hypothesis about the mechanism of the mononuclear heterocyclic rearrangements.
Free‐radical reactions of diazonium salts with α,β‐unsaturated carbonyl compounds. A new synthesis of 1,4‐diarylpyrazole derivatives
Authors: Citterio Attilio , Ramperti Massimo , Vismara Elena 
Published: March 2009

AbstractFree‐radical decomposition of diazonium salts catalyzed by titanous or titanous and ferrous salts in the presence of β‐substituted α,β‐unsaturated carbonyl compounds leads to 1,4‐diarylpyrazole derivatives. The reaction occurs via an intermediate azo compound (1), which can be reduced by the metal salt or can be isolated and hydrogenated to pyrazole derivatives.
Novel heterocycles. 8. Fused isoquinolines derived from the reaction of homophthalic anhydride with cyclic imino ethers
Authors: Coppola Gary M. 
Published: March 2009

AbstractHomophthalic anhydride and cyclic imino ethers react to produce fused isoquinolines 6–9. In the case of 2‐ethoxy‐2‐oxazoline, a second compound whose structure is believed to be the spiro compound 10 was also isolated. Spectral data for these type systems are discussed.
Synthesis of 5‐ethynylorotic acid
Authors: Bhatt Ram S. , Kundu Nitya G. , Chwang T. Ling , Heidelberger Charles 
Published: March 2009

AbstractCondensation of 2,4‐dimethoxy‐5‐iodo‐6‐carbomethoxypyrimidine (10) with copper (I) 3‐tetrahydropyranyloxyprop‐1‐ynide (4) afforded 2,4‐dimethoxy‐5‐(3′‐tetrahydropyranyloxyprop‐1′‐yn)‐6‐carbomethoxypyrimidine (11), which was hydrolyzed to produce 2,4‐dimethoxy‐5‐(3′‐hydroxyprop‐1′‐yn)‐6‐carbomethoxypyrimidine (12). Oxidation of 12 with dimethyl sulfoxide‐oxalyl chloride reagent gave the acetylenic aldehyde (13), which on treatment with sodium methoxide in dry tetrahydrofuran yielded 2,4‐dimethoxy‐5‐ethynyl‐6‐carbomethoxypyrimidine (14). The trimethylsilyl derivative (15) was deprotected by sequential treatment with iodotrimethylsilane and aqueous sodium hydroxide, leading to the formation of 5‐ethynylorotic acid (1).
Pipérazinediones‐2,5. 2. Les acides dioxothiazolidino pipérazine carboxyliques et leurs dérivés désulfurés
Authors: Jerumanis Stanislas , Lemieux Alain 
Published: March 2009

AbstractLes auteurs ont synthétisé l'acide N‐t‐butoxycarbonylglycyl‐3 méthoxycarbonyl‐4 diméthyl‐5,5 thiazolidine carboxylique‐2 (5) à partir de trois différents produits de départ (Schéma 1). Ce produit 5 at été transformé en diméthyl‐2,2 dioxo‐5,8 thiazolidino[3,2‐a]pipérazine carboxylate‐3 de méthyle (7) puis hydrolysé en acide cor‐respondant 8 avec un rendement quantitatif. Par désulfuration réductrice, le produit 8 ainsi que son isomère, le diméthyl‐1,1, dioxo‐5,8 thiazolidino[3,4‐a]pipérazine carboxylate‐3 de butyle (10) ont été transformés en nouveaux dérivés de la pipérazinedione‐2,5, soit l'acide(dioxo‐2,5 pipérazinyl)‐2 isobutyrique (9) et l'(isopropyl‐2 dioxo‐3,6 pipérazinyl‐1) acétate de butyle (11). Les données spectroscopiques sont conformes aux structures des produits obtenus.
Reactions of 2‐chloro‐2‐(4‐pyridyl)propane with nucleophiles. Substitution on tertiary carbon
Authors: Feuer Henry , Doty James K. , Kornblum Nathan 
Published: March 2009

AbstractThe reaction of 2‐chloro‐2‐(4‐pyridyl)propane (2) with lithium 2‐propanenitronate affords the C‐alkylation product 2‐nitro‐3‐(4‐pyridyl)‐2,3‐dimethylbutane (3), the Michael‐adduct 2‐nitro‐2‐methyl‐4‐(4‐pyridyl)pentane (4), 4‐isopropenylpyridine (5) and 2‐(4‐pyridyl)‐2‐propanol (6). Of these four products, only the formation of 3 is suppressed when the reaction is performed in the presence of radical inhibitors. The reaction of compound 2 with sodium azide gives the tertiary substitution product 2‐azido‐2‐(4‐pyridyl)propane (8). The reaction is not influenced by radical inhibitors. This is also the case in the reaction of 2 with sodium benzenethiolate, which affords 2‐mercaptophenyl‐2‐(4‐pyridyl)propane (9) and 1‐mercaptophenyl‐2‐(4‐pyridyl)propane (10). Compound 5, the product of an E2‐type elimination is also formed in the azide and thiolate reactions. A Michael type addition of sodium benzenethiolate to 5 explains the formation of 10. Similarly, generation of 5 in reactions of 2 with sodium methanethiolate and sodium cyanide accounts for the formation of 1‐mercaptomethyl‐2‐(4‐pyridyl)propane (11) and 3‐(4‐pridyl)butanenitrile (12), respectively.
Dilithiation of 1‐benzenesulfonylindoles
Authors: Sundberg Richard J. , Broome Rita , Walters Claudia Powers , Schnur Dora 
Published: March 2009

AbstractBenzenesulfonylindole is converted to a dilithio derivative by 2.2 equivalents of lithiating reagent. The dilithio derivative gives rise to sultones on reaction with carbonyl compounds. This reaction proceeds by an intramolecular displacement of the indole group from the bis‐adduct. Fair to poor yields of the 2‐indolycarbinols can also be isolated. Benzoyl chloride forms a thiazine dioxide ring by addition at both the 2‐indolyl and 2′‐phenylsulfonyl positions. 3‐Methyl‐1‐benzenesulfonylindole is also easily dilithiated.
Synthesis of 2,3‐dihydrospiro[benzofuran‐2,4′ ‐piperidines] and 2,3‐dihydrospiro[benzofuran‐2,3′‐pyrrolidines]
Authors: Effland Richard C. , Gardner Beth Ann , Strupczewski Joseph 
Published: March 2009

AbstractThe synthesis of 2,3‐dihydrospiro[benzofuran‐2,4′‐piperidines] 3 and 2,3‐dihydrospiro[benzofuran‐2,3′]‐pyrrolidine] 6 is described. The synthesis was achieved by a Grignard reaction of a 2‐fluorobenzylhalide with an appropriate cycloazaalkyl ketone to yield the tertiary alcohols 1 and 4. Subsequent intramolecular displacement of the aromatic fluoride by the derived alkoxides provided the novel system.Nitration of 1′‐acetyl‐2,3‐dihydrospiro[benzofuran‐2,4′‐piperidine] 7 resulted in a 5‐nitro derivative.
Heterocyclic systems. II. Synthesis of 4H,6H‐pyrrolo[1,2‐a][4,1]benzoxazepine
Authors: Massa Silvio , Corelli Federico , Stefancich Giorgio 
Published: March 2009

AbstractThe reduction of 1‐(2‐methoxycarbonylphenyl)pyrrole‐2‐carboxaldehyde by lithium aluminum hydride led to 1‐(2‐hydroxymethylphenyl)‐2‐hydroxymethylpyrrole, which was in turn transformed into 4H,6H‐pyrrolo‐[1,2‐a][4,1]benzoxazepine through intramolecular dehydration. The reductive action of sodium borohydride, instead, allowed the preparation of 6‐oxo‐4H‐pyrrolo[1,2‐a][4,1]benzoxazepine.
A short synthesis of 5‐methylhistamine
Authors: Pfister Jürg R. , Kurz Walter , Harrison Ian T. 
Published: March 2009

AbstractMethoxybromination of 4,5‐dihydro‐2‐methylfuran (4), followed by treatment of the resulting bromoketal 5 with hot formamide, gave 4‐(2‐hydroxyethyl)‐5‐methyl‐1H‐imidazole (3) in 25% yield. This method provides easy access to the selective H2‐agonist 4‐methylhistamine (1) via the chloromethyl intermediate 2.
Notes on the synthesis of meso‐substituted porphyrins from pyrryl carbinols and the mechanism of the rothemund reaction
Authors: Little Robert G. 
Published: March 2009

AbstractAryl pyrryl carbinols have been found to readily cyclize to meso‐substituted tetraarylporphyrins in yields which are consistent with the intermediacy of the pyrryl carbinols in the Rothemund reaction. Acidic solutions of the pyrryl carbinols show absorption bands characteristic of pyrrolylmethenes. It is suggested that pyrrolylmethenes are likely intermediates in the Rothemund reaction.