HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 24, No. 3, 1986
Published online:
■ Synthesis of Naturally Occuring 2,5-Dialkylchromones. Part 1. Synthesis of Aloesone and Aloesol
Paola Gramatica, M. Pia Gianotti, Giovanna Speranza, and Paolo Manitto*
*Dipartimento di Chimica Organica e Industriale, Università digli Studi di Milano, via Golgi 19, I-20133 Milano, Italy
Abstract
A number of 2-alkyl-7-alkoxy (or hydroxy)-5-methylchromones, including naturally occurring aloesone and aloesol, were synthesized starting from ethyl orsellinate via β-ketosulfoxides as intermediates.
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■ Synthesis of Spiro[3,4,5,6-tetrahydro-1,4-oxazin-2-one-6,2’-tricyclo[3.3.1.13,7]decane]
Vassil St. Georgiev,* George B. Mullen, and Christopher G. Acker
*Department of Organic Chemistry, Pharmaceutical Division, Pennwalt Corporation, Rochester, New York 14623, U.S.A.
Abstract
The synthesis of spiro[3,4,5,6-tetrahydro-1,4-oxazin-2-one-6,2’-tricyclo[3.3.1.13,7]decane], a novel heterocyclic system ie described.
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■ Preparation of 3-Substituted Quinolines. II. Preparation and Cyclodehydration of α-Alkyl- and α-Pheyl-β-arylaminoacrolein Derivatives
Reiko Todoroki, Machiko Ono, and Shinzo Tamura*
*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan
Abstract
α-Methyl-β-arylaminoacroleins were prepared by the hydrolysis of 2-methyl-1-arylamino-3-arylimino-1-propene derivatives. α-Ethyl- and α-phenyl-β-arylaminoacroleins were prepared by the reaction of arylamines and 2-substituted 1,1,3,3-tetraethoxypropane derivatives. 3-Methyl-, 3-ethyl- and 3-phenylquinolines were obtained from α-methyl-, α-ethyl and α-phenyl-β-arylaminoacroleins on heating with aluminum bromide in good yields. α-Bromo-β-anilinoacrolein (9b) was prepared by the reaction of β-anilinoacrolein (6b) and N-bromosuccinimide. Reaction of 9b and aluminum bromide did not afford 3-bromoquinoline.
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■ A Versatile Novel Synthesis of Benzofuran and Related Compounds. II. The Vilsmeier Reaction of α-Phenoxyacetophenones
Takashi Hirota,* Hiroko Fujita, Kenji Sasaki, Tetsuto Namba, and Shohei Hayakawa
*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
A novel synthesis of 2-benzoylbenzofurans by the Vilsmeier reaction of α-phenoxyacetophenones are described.
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■ Synthetic Approach to the Antitumour Antibiotics Neothramycins
Nicole Langlois,* Philippe Bourrel, and Ratremaniaina Z. Andriamialisoa
*Institut des Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France
Abstract
A new simple synthetic route to the pyrrolo[1,4]benzodiazepines (5) related to the neothramycins (1) and (2) through the methyl imidate (7) is described.
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■ Coupling Reaction of Chloropyrazines and Their N-Oxides with Tetraphenyltin
Akihiro Ohta,* Masakatsu Ohta, and Tokuhiro Watanabe
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
By the coupling reaction of monochloropyrazines, dichloropyrazines, 2-chloropyrazine 1-oxides, and 2-chloropyrazine 4-oxides with tetraphenyltin, the corresponding phenylpyrazines were prepared in satisfactory yields.
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■ Pyridazines XXXI. A Facile Synthesis of 3-Pyridazinecarbonitriles via 2-(4-Toluenesulfonyl)-2,3-dihydro-3-pyridazinecarbonitriles
Wolfgang Dostal and Gottfried Heinisch*
*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria
Abstract
Pyridazines 1a-c react with trimethylsilyl cyanide/4-toluenesulfonyl chloride to give 2-(4-toluenesulfonyl)-2,3-dihydro-3-pyridazinecarbonitriles (2a-c) in satisfactory yields. Conversion of compounds 2a-c into 3-pyridazinecarbonitriles 3a-c is conveniently accomplished by action of 1,8-diazabicyclo[5.4.0]undec-7-ene.
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■ Photoreaction of 4-Iodopyridine with Heteroaromatics
Koh-ichi Seki,* Kazue Ohkura, Masanao Terashima, and Yuichi Kanaoka
*Faculty of Pharmaceutical Scicences, Higashinihonngakuen University, 1757 Kanazawa, Toubetu-cho, Ishikari-gun, Hokkaodo 061-0212, Japan
Abstract
Photoreaction of 4-iodopyridine with various heteroaromatics leads to give the corresponding 4-heteroarylpyridines in appreciable yields.