Cycloaddition Reactions of N-Benzotriazolylketene as a Heteroarylketene: A Practical Approach to the Synthesis of Novel Azetidinones

Fatemeh Zigheimat; Mohammad Reza Islami; Farahnaz Nourmohammadian

doi:10.1055/s-0033-1340280

Synlett, Table of Contents

Synlett 2014; 25(2): 229-232
DOI: 10.1055/s-0033-1340280

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Cycloaddition Reactions of N-Benzotriazolylketene as a Heteroarylketene: A Practical Approach to the Synthesis of Novel Azetidinones

Fatemeh Zigheimat

^aDepartment of Chemistry, Shahid Bahonar University of Kerman, 76169, Kerman, Iran Fax: +98(341)3222033 Email: mrislami@uk.ac.ir

,

Mohammad Reza Islami*

^aDepartment of Chemistry, Shahid Bahonar University of Kerman, 76169, Kerman, Iran Fax: +98(341)3222033 Email: mrislami@uk.ac.ir

,

Farahnaz Nourmohammadian

^bDepartment of Organic Colorants, Institute for Color Science and Technology, 654-16765, Tehran, Iran

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Abstract

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Abstract

A series of novel functionalized azetidinones containing the benzotriazole moiety were synthesized stereoselectively by a reaction of benzotriazolylacetic acid, aromatic amines, and Mukaiyama’s reagent in the presence of triethylamine in dichloromethane at ambient temperature. This transformation generates a four-membered lactam and presumably proceeds via in situ generation of benzotriazolylketene as a heteroarylketene. In contrast to the products obtained from the reaction of pyrrolylketene with imines in which cis-azetidinones were formed as major products, the generated benzotriazolylyketene reacted with imines forming the trans-lactams as major products.

Key words

ketenes - Schiff bases - N-benzotriazolylketene - [2π+2π] cycloaddition - azetidinones

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