Tetrahedron

Samarium diiodide promoted formation of 1, 2-diketones and 1-acylamido-2-substituted benzimidazoles from N-acylbenzotriazoles

X Wang, Y Zhang

Index: Wang, Xiaoxia; Zhang, Yongmin Tetrahedron, 2003 , vol. 59, # 23 p. 4201 - 4207

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Citation Number: 34

Abstract

N-Acylbenzotriazoles, when treated with samarium diiodide in THF, undergo self-coupling reaction to afford 1, 2-diketones in good to excellent yields; while when treated with samarium diiodide in CH3CN, they undergo ring-opening reaction to afford 1-acylamido-2- alkyl (or aryl) benzimidazoles in reasonable to good yields. A plausible mechanism was suggested.

~90%

~54%

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~73%

~63%

~53%

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~36%

~15%

~29%

~90%

~61%

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