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Syntheses of 2,3-dicyano-5a,8a-dihydro-5a-hydroxycyclopentano[1′,2′:4,5]pyrrolo[2,3-b]pyrazines and 2,3-dicyanocyclohexano[1′,2′:4,5]pyrrolo-[2,3-b]pyrazines

✍ Scribed by Kazuko Shirai; Koushi Fukunishi; Dongfeng Hou; Masaru Matsuoka

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
450 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Previously synthesized 2‐(3′‐chloro‐5′,6′‐dicyanopyrazin‐2′‐yl)cyclopentan‐1‐one 1, obtained from the reaction of 2,3‐dichloro‐5,6‐dicyanopyrazine with 1‐pyrrolidino‐1‐cyclopentene, was further reacted with primary alkylamines to give mixtures of diastereomer of 5‐alkyl‐2,3‐dicyano‐5a,8a‐dihy‐dro‐5a‐hydroxycyclopentano[1′,2′:4,5]pyrrolo[2,3‐b]pyrazines 3a‐h in high yield. The reaction of 2‐alkylamino‐3‐chloro‐5,6‐dicyanopyrazine with 1‐pyrrolidino‐1‐cyclohexene gave 5‐alkyl‐2,3‐dicyanocyclopentano[1′,2′:4,5]pyrrolo[2,3‐b]pyrazines 5a‐b together with 5‐alkylamino‐2,3‐dicyano‐6‐pyrrolidinopyrazines 6a‐b. The products prepared are all of interest as potential pesticides and new fluorescent chromophores.

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