N,N-bond-forming heterocyclization: synthesis of 3-alkoxy-2H-indazoles

Aaron D Mills; Musa Z Nazer; Makhluf J Haddadin; Mark J Kurth

doi:10.1021/jo0524831

N,N-bond-forming heterocyclization: synthesis of 3-alkoxy-2H-indazoles

J Org Chem. 2006 Mar 31;71(7):2687-9. doi: 10.1021/jo0524831.

Authors

Aaron D Mills¹, Musa Z Nazer, Makhluf J Haddadin, Mark J Kurth

Affiliation

¹ Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA.

PMID: 16555821
DOI: 10.1021/jo0524831

Abstract

A one-step heterocyclization of o-nitrobenzylamines to 3-alkoxy-2H-indazoles is reported. The electronic nature of the nitrophenyl group, the steric and electronic nature of the R1-functionalized benzylic amine, and the nature of the alcoholic solvent affect the efficiency of this heterocyclization reaction (approximately 40-90%).

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cyclization
Indazoles / chemical synthesis*
Indazoles / chemistry
Molecular Structure
Stereoisomerism

Substances

Indazoles