Cyclization of 1-(2-alkynylphenyl)-3, 3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles

DB Kimball, TJR Weakley…

Index: Kimball, David B.; Weakley, Timothy J. R.; Haley, Michael M. Journal of Organic Chemistry, 2002 , vol. 67, # 18 p. 6395 - 6405

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Citation Number: 62

Abstract

A new route to isoindazoles and cinnolines through the cyclization of (2-alkynylphenyl) triazenes under neutral conditions is presented. The products that result from heating the starting triazenes depend on both the type of alkyne ortho to the triazene functionality and the temperature used. Butadiyne moieties ortho to dialkyltriazenes yield bis-isoindazole dimers when heated to 150° C in MeI. A requirement for cyclization in MeI is that the (2- ...