Synthesis of 2H-Indazoles via Lewis Acid Promoted Cyclization of 2-(Phenylazo)benzonitriles

Lewis-acid promoted “coarctate” cyclization of 10 2-(phenylazo)benzonitrile derivatives furnishes the isoindazole ring system in ca. 65−95% yield. A plausible mechanism for this unusual transformation is proposed.

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Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (17), p.6619-6622
Main Authors: Shirtcliff, Laura D, Rivers, Jazmin, Haley, Michael M
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Description
Summary:Lewis-acid promoted “coarctate” cyclization of 10 2-(phenylazo)benzonitrile derivatives furnishes the isoindazole ring system in ca. 65−95% yield. A plausible mechanism for this unusual transformation is proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060965m