Tetrahedron letters

Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer-bound esters

H Matsushita, SH Lee, M Joung, B Clapham…

Index: Matsushita, Hana; Lee, Sang-Hyeup; Joung, Meyoungju; Clapham, Bruce; Janda, Kim D. Tetrahedron Letters, 2004 , vol. 45, # 2 p. 313 - 316

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Citation Number: 125

Abstract

The preparation of an array of benzimidazoles and benzothiazoles from polymer-bound esters is described. Polymer-bound esters were treated with 2-aminothiophenols or 1, 2- phenylenediamines in the presence of a Lewis acid to afford the corresponding benzothiazole or benzimidazole cleavage products. The reaction of 2-aminophenols with the polymer-bound esters failed to give the desired benzoxazole products using this ...

~46%

~20%

~63%

~47%

~71%

~63%

~41%

~48%

~77%

~98%

~71%

~43%

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~75%

~48%

~97%

~72%

~37%

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~58%

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~45%

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