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Studies on Heteropentalenes. V. : Cycloadditions of 5-Aryl-3-methylimidazo[5,1-b]thiazoles with acetylenic Esters Leading to 5-Aryl-3-methyl-thiazolo[2,3-c]benzimidazoles and Related Heterocycles

Bulletin of the Chemical Society of Japan Volume 55 Issue 8 Page 2464-2469
published_at 1982
Title
Studies on Heteropentalenes. V. : Cycloadditions of 5-Aryl-3-methylimidazo[5,1-b]thiazoles with acetylenic Esters Leading to 5-Aryl-3-methyl-thiazolo[2,3-c]benzimidazoles and Related Heterocycles
Creators Abe Noritaka
Creators Nishiwaki Tarozaemon
Creators Ikeda Kotaro
Cycloaddition of 5-aryl-3-methylimidazo[5,1-b]thiazoles with dialkyl acetylenedicarboxylate in an aprotic nonpolar solvent gives a number of products including epimeric thiazolo[2,3-c]benzimidazoles (3 and 4) [1:2-cycloadducts], epimeric 5,10b-ethenothiazolo[3',2':3,4]imidazo[1,5-a]-pyridines (5 and 6) [1:3-cycloadducts], and thiazolo[3',2':3,4]imidazo[1,2-a]pyridines [1:3-adducts]. At higher temperature, formation of the 1:2-cycloadducts is favored over the 1:3-adducts, whereas the latter predominates at room temperature. In an aprotic polar medium, the 1:3-cycloadducts (5 and 6) and tetraalkyl 6-arylpyridine-2,3,4,5-tetracarboxylates are substantially produced. Epimerization of 3 and 4 has been found to compete well with fragmentation to 4H-1,4-benzothiazine.
Languages eng
Resource Type journal article
Publishers 日本化学会
Date Issued 1982
File Version Not Applicable (or Unknown)
Access Rights metadata only access
Relations
[ISSN]0009-2673
[NCID]AA00580132
https://doi.org/10.1246/bcsj.55.2464
[isPartOf] [URI]http://www.jstage.jst.go.jp/browse/bcsj/-char/en
Schools 大学院医学系研究科(理学)