Studies on Heteropentalenes. IV. Heteroannelations to Pyrrolo-[2,1-<I>b</I>]benzothiazole and Pyrrolo[2,1-<I>b</I>]thiazoles
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概要
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2,3-Dibenzoylpyrrolo[2,1-<I>b</I>]benzothiazole (<B>2</B>) and 6,7-dibenzoylpyrrolo[2,1-<I>b</I>]thiazoles (<B>5a</B>–<B>b</B>) have been synthesized by utilizing the cycloaddition reactions of imidazo[2,1-<I>b</I>]benzothiazole and imidazo[2,1-<I>b</I>]thiazoles, respectively, with dibenzoylacetylene followed by the elimination of a nitrile from each of the cycloadducts. Heteroannelations to <B>2</B> and <B>5</B> have been achieved by their reactions with hydrazine, aminoacetonitrile, ethyl glycinate, and phosphorus pentasulfide. The annelations by the second and third reagents proceed fairly regioselectively. Facile dimerizations of thieno[3′,4′:3,4]pyrrolo[2,1-<I>b</I>]benzothiazole and thieno[3′,4′:3,4]pyrrolo[2,1-<I>b</I>]thiazoles to be produced by the reactions with the last reagent are also described.
- 公益社団法人 日本化学会の論文
著者
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Abe Noritaka
Department Of Pure And Applied Chemistry Faculty Of Science And Technology Tokyo University Of Scien
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Harada Emiko
Department of Chemistry, Faculty of Sciences, Yamaguchi University
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Nishiwaki Tarozaemon
Department of Chemistry, Faculty of Sciences, Yamaguchi University
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Omori Toshimasa
Department of Chemistry, Faculty of Sciences, Yamaguchi University
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Nishiwaki Tarozaemon
Department of Chemistry, Faculty of Science, Yamaguchi University
関連論文
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- Studies on heteropentalenes. II. Cycloaddition of imidazo(2,1-b)thiazoles, thiazolo(3,2-a)benzimidazole, and imidazo(2,1-b)benzothiazole with a reactive acetylenic ester.
- Studies on heterocyclic analogs of azulenes. XI. Syntheses and cycloadditions of cyclohepta(4,5)pyrrolo(1,2-a)imidazoles and cyclohept(d)imidazo(1,2-a)imidazoles.
- Studies on heterocyclic analogs of azulene. VI. Cycloadditions of styryl-substituted aza analogs of azulene with dimethyl acetylenedicarboxylate.
- Studies on heterocyclic analogs of azulene. VIII. Reaction of 2-alkoxycyclohepta(b)pyrroles with dimethyl acetylenedicarboxylate.
- Studies on heterocyclic analogs of azulenes. III. The reactions of 2-chloro-3-ethoxycarbonylcyclohepta[b]pyrrole with the carbanions derived from active methylene compounds.
- Studies on heterocyclic analogs of azulene. VII. Regioselective cycloadditions of cycloheptimidazole to electron-deficient olefins.