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Phenanthrene-fused azo-ene-ynes: synthesis of dibenzo[f,h]cinnoline and dibenzo[e,g]isoindazole derivatives.

ABSTRACT: The cyclization reactions of a phenanthreno-fused azo-ene-yne compound have been studied both experimentally and computationally. Experimental results show that this system is prone to dimerization, more so than previously studied naphthalene- and benzene-based analogues. Calculations reveal that pyrazoles and arene-fused pyrazoles strongly stabilize carbenes in the 5-position through "coarctate conjugation", suggesting a stationary concentration of the carbenes/carbenoids during cyclization that is high enough for dimerization.

SUBMITTER: Young BS

PROVIDER: S-EPMC3888224 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Phenanthrene-fused azo-ene-ynes: synthesis of dibenzo[f,h]cinnoline and dibenzo[e,g]isoindazole derivatives.

Young Brian S BS Köhler Felix F Herges Rainer R Haley Michael M MM

The Journal of organic chemistry 20110922 20

The cyclization reactions of a phenanthreno-fused azo-ene-yne compound have been studied both experimentally and computationally. Experimental results show that this system is prone to dimerization, more so than previously studied naphthalene- and benzene-based analogues. Calculations reveal that pyrazoles and arene-fused pyrazoles strongly stabilize carbenes in the 5-position through "coarctate conjugation", suggesting a stationary concentration of the carbenes/carbenoids during cyclization tha ...[more]

PMID: 21939200

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