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. 22, No. 10, 1984
Published online:
■ Isolation and Structures of Three Seco-limonoids, Insect Antifeedants from Trichilia roka (Meliaceae)
Munehiro Nakatani,* Miyako Okamoto, Takashi Iwashita, Kosei Mizukawa, Hideo Naoki, and Tsunao Hase
*Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan
Abstract
The stem bark of African medicinal plant Trichilia roka has been found to contain a number of limonoids. Three of these has been isolated as insect antifeedant; They are all of the ring B-cleaved meliacan group and are closely related to known prieurianin.
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■ Ring Transformations of a Thiazoline Fused δ-Lactone into a γ-Lactam and a 1,4-Thiazinone
Alessandro Dondoni,* Giancarlo Fantin, Marco Fogagnolo, and Alessandro Medici
*Department o f Organic Chemistry, University of Ferrara, Via Fossato di Mortara, 17/19, I-44100 Ferrara, Italy
Abstract
The thiazoline fused δ-lactone 1 is converted via the methyl N-acyl-2-ethanoate 2a into the N-vinylthiazinone 3 or the thiazoline fused γ-lactam 4.
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■ Photo-arylation III: Synthesis of 2-Heteroarylpyridines
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
The title compounds were prepared in satisfactory yields by photo-reaction of 2-halopyridine (halogen; I, Br) with five membered heteroaromatics.
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■ Alkylation of Cyclic Gem-dinitrosamines
Joseph Henry Boyer* and Govindarajulu Kumar
*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.
Abstract
Alkylations with benzaldehyde catalyzed by potassium tert-butoxide converted 1,3,5-trinitrosohexahydro-1,3,5-triazine 1, 1,3-dinitrosoimidazolidine 3 and 1,3-dinitrosohexahydropyrimidine 4 to the 2-hydroxybenzyl derivatives (76 - 88%) and, in one instance, to the dialkylated product, 2,4-di-(hydroxybenzyl)-1,3,5-trinitrosohexahydro-1,3,5-triazine (40%). Lithium diisopropylamide was a less effective catalyst in alkylations with benzaldehyde or methyl iodide and was converted to diisopropylnitrosamine by transnitrosation. A catalytic amount of triethylbenzylammonium chloride promoted efficient mono-α-benzylations of nitrosamines 3 and 4 in aqueous sodium hydroxide at 25°C; however, simple nitrosamines failed to react and the trinitrosamine 1 was decomposed by the alkaline medium.
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■ Synthesis of Pyrazolo[3,4-d]pyridazines — Thionation Followed by Alkylation of Pyrazolo[3,4-d]pyridazin-4(5H)-one
Kenji Kaji, Hiromu Nagashima, Keizo Tabashi, and Hirohisa Oda*
*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan
Abstract
Alkylation of the pyrazolo[3,4-d]pyridazine-4(5H)-thiones are described. Employment of an equivalent of alkylating agent afforded only S-alkylated products, while S,N-dialkyl compounds were formed when an excess of alkylating agent was used. An unequivocal synthesis and 1H-NMR spectroscopic studies of 1- and 2-alkyl-4-alkylthiopyrazolo[3,4-d]pyridazines are also discussed.
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■ 1,3-Dipolar Cycloaddition of Aryl Azides with 5-Alkoxy-3-pyrrolin-2-ones. Synthesis of 4-Alkoxy-6-aryl-3,6-diazabicyclo[3.1.0]hexan-2-ones
Yoshiyuki Kosugi* and Fumiko Hamaguchi
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
1,3-Dipolar cycloaddition of p-bromophenyl azide with 5-ethoxy-3-pyrrolin-2-one (2a) gave a regioisomeric mixture of triazolines. While thermal decomposition of the triazolines (3a,4a) afforded aziridine (10a) and enamines (12,13), 3a and 4a underwent photo-decomposition to give the aziridine [6-(4-bromophenyl)-4-ethoxy-3,6-diazabicyclo[3.1.0]hexan-2-one (10a)] exclusively.
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■ One-pot Selective Acylation of Amines Using 3,6-Diethyl-2-hydroxypyrazine as Acyl Carrier
Akihiro Ohta,* Yukiko Inagawa, Yukari Okuwaki, and Makoto Shimazaki
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
Introduction of 3,6-diethyl-2-hydroxypyrazine into a system of amide syntheses using acyl diethylphosphates resulted in the performance of selective acylation in satisfactory yields.
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■ Cyanation in the Pyridine Series: Synthetic Applications of the Reissert-Henze and Related Reactions
Wilmer K. Fife* and Eric F. V. Scriven
*Department of Chemistry, Indiana-Purdue University, PO Box 647, Indianapolis, IN 46223, U.S.A.
Abstract
This review provides an up-to-date summary of the Reissert-Henze reaction, as applied to the cyanstion of pyridine derivatives. It highlights recent studies that have established some highly efficient, regioselective methods for the synthesis of 2- and 4-pyridinecarbonitriles.