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. 3, No. 9, 1975
Published online:
■ A Facile Synthesis of 2,3-Dihydro-1H-pyrrolo[1,2-a]indoles
Tetsuji Kametani,* Kimio Takahashi, Masataka Ihara, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Cyclisation of α-(2-bromophenyl)-δ2,α-pyrrolidineacetonitriles (4 and 13) with sodium hydride and cuprous bromide in dimethylformamide gave quantitatively the corresponding pyrrolo[l,2-a]indoles (5 and 14), which were converted into the aldehydes (6 and 15).
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■ Nitrogen Inversion in Solasodine N-Methyl and N-Formyl Derivatives
Genjiro Kusano, Tsunematsu Takemoto,* Norio Aimi, Herman J. C. Yeh, and David F. Johnson
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
O-Acetyl-N-methylsolasodine A (III) and B (IV), O-Acetyl-N-formylsolasodine A (V) and B (VI) are prepared. III and IV are interconvertible under acidic condition or at high temperature. Procedure of recrystallization of the mixture of III and IV precipitates III alone. V are reduced to N-methylsolasodine B (XI), while VI are reduced to a mixture of N-methylsolasodine A (X) and B (XI). These isomers are described as a result of nitrogen inversion.
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■ Photochemical Reactions of 3-N,N-Diethylaminocyclobut-2-en-1-ones
Takehiko Nishio, Hiromu Aoyama, and Yoshimori Omote*
*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan
Abstract
Irradiation of 3-N,N-diethylamino-bphenyl-cyclobut-2-en-1-one (I) in methanol afforded two kinds of β-keto esters III and IV. While irradiation of 2,4-diphenyl-3-N,N-diethylamino-cyclobut-2-en-one (II) in benzene gave a furan derivative V.
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■ Transformations of 1,3-Disubstituted Uracil-carbene Adducts Ring Expansion to 1,3-Diazepine Derivatives
Herman P. M. Thiellier, Gerrit-Jan Koomen, and Upendra K. Pandit*
*Organic Chemistry Laboratory, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
Abstract
A facile conversion of uracil-carbene adducts (1) to diazepinediones (2) is described.
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■ N-Benzoyloctahydro-7(1H)-quinolone. Exclusive Isomerization of the Ring Junction to Cis rather than Trans Fusion
Takefumi Momose,* Shuji Uchida, Noriko Yamaashi, and Takeshi Imanishi
*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan
Abstract
The synthesis and stereochemistry of trans- and cis-octahydro-7(1H)-quinolones are described. There was found a marked stability of cis- rather than trans-configuration of N-benzoyloctahydro-7(1H)-quinolone system.
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■ Photoaddition Reactions of N-Methylphthalimide with Toluenes and Amines
Yuichi Kanaoka,* Kazuko Sakai, Ryuji Murata, and Yasumaru Hatanaka
*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Abstract
Photoreactions of N-methylphthalimide 1 were examined in presence of substituted toluenes and tertiary amines. Together with the reduced products 3, 5, 6, the addition products 2, 4, were obtained. It has been shown that the imide carbonyl is capable of photochemically adding the methylene adjacent to benzene and nitrogen.
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■ Reaction of 2-Aminobenzoxazole with Diketene
Tetsuzo Kato,* Takuo Chiba, and Mohsen Daneshtalab
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
2-Aminobenzoxazole reacts with diketene to give the related N-acetoacetyl, and pyrimido[1,2-a]benzoxazol-4-one derivatives in good yield. Ring closure reaction of the N-acetoacetyl derivative (IIIa), and other reactions are described.