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. 6, No. 12, 1977
Published online:
■ Photo-oxygenation of 8-Methoxyberberinephenolbetaine. A Novel Synthesis of Spirobenzylisoquinoline System from Berberine
Miyoji Hanaoka* and Chisato Mukai
*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan
Abstract
Photo-oxygenation of 8-methoxyberberinephenolbetaine(I1) afforded the spirobenzylisoquinoline (III), the imide-ester (IV). and methoxyberberal (V). Acidic hydrolysis of III yielded the diketospirobenzylisoquinoline (VII).
Published online:
■ A Novel Method for the Preparation of Substituted Enaminoketones
Tsunetoshi Honma* and Yukio Tada
*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan
Abstract
A novel method for the preparation of enaminoketones, which consists of the condensation of various heteroaromatic cyano compounds with ketones in the presence of base, such as sodium amide or sodium hydride is described. The enaminoketones can easily be converted to the corresponding β-diketones and heterocyclic compounds, such as isothiazole, isoxazole, pyrazole, pyrimidine, and thiazole.
Published online:
■ A Novel Cleavage of the Methlenedioxy Group during the Photochemical Synthesis of Aporphines
Bantwal R. Pai,* Hosbett Suguna, Sakaran Natarajan, and Govindarajan Manikumar
*Department of Chemistry, Presidency College, Madras 600005, India
Abstract
Irradiation of 1-(2-bromo-5-hydroxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline (1) in 2% aqueous sodium hydroxide solution gives (±)-roemeroline (2) and 2,9-dihydroxyaporphine (3). Similarly 1-(2-bromo-5-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline (5) leads to (±)-cassythicins (6) and 2,9-dihydroxy-10-methoxyaparphine (7). These are the first examples of the cleavage of methylenedioxy groups during photolysis in an alkaline medium.
Published online:
■ The Synthesis of Some 2-Substituted 5-Nitropyrimidines
Derek T. Hurst* and John Christophides
*School of Analytical and Biological Chemistry, Kingston Polytechnic, Kingston-on-Thames, KT1 2EE, U.K.
Abstract
The synthesis of 2-(fur-2-yl)-, 2-(5-nitrofur-2-yl)-, 2-(N-morpholinyl)-, and 2-methylsulphonyl-5-nitropyrimidine is described together with the synthesis of some other 2-(substituted) 5-nitropyrimidines. 2-(N-Morpholinyl)- and 2-(fur-2-yl)-5-nitropyrimidine were reduced to the corresponding 5-amino derivatives.
Published online:
■ The Synthesis of Some Halogenopyrimidines and Some Routes to Cyanopyrimidines
Derek T. Hurst,* Keith Biggadike, and Jefferey J. Tibble
*School of Analytical and Biological Chemistry, Kingston Polytechnic, Kingston-on-Thames, KT1 2EE, U.K.
Abstract
The syntheses of a number of new halogenopyrimidines related to commercially available agricultural chemicals are described. Some further reactions of these compounds are recorded and routes to some new cyanopyrimidines are outlined. The synthesis of 2-chloro-4,6-dicyanopyrimidine, the second recorded dicyanopyrimidine, is reported.
Published online:
■ A New Synthesis of Doryanine and Related Isocarbostyril
Hideo Iida,* Nobuko Katoh, Mamoru Narimiya, and Toyohiko Kikuchi
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
Doryanine was synthesised in one step from 3,4-methylenedioxyhomophthalimide derivative.
Published online:
■ Photochemistry as a Tool in Heterocyclic Synthesis. From Pyridinium N-Ylides to Diazepines and Beyond
Jacques Streith*
*Ecole Nationale Supérieure de Chimie de Mulhouse, Université du Haut-Rhin, 68093 Mulhouse, France
Abstract
In the first part of this review we shall describe some industrial applications of photoinduced heterocyclic syntheses via singlet oxygen and via free radicals. The second part is dealing with large bench-scale synthesis of 1,2-diazepines which are thence used as building stones for the synthesis of some new polyheterocyclic systems.