One-Carbon Homologation of Aldehydes to N-(α-Haloacyl)benzotriazoles

Alan R. Katritzky; Srinivasa R. Tala; Sandeep K. Singh

doi:10.1055/s-2006-950183

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Synthesis 2006(19): 3231-3237
DOI: 10.1055/s-2006-950183

PAPER

One-Carbon Homologation of Aldehydes to N-(α-Haloacyl)benzotriazoles

Alan R. Katritzky*, Srinivasa R. Tala, Sandeep K. Singh
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;

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Publication History

Received 27 April 2006
Publication Date:
15 August 2006 (online)

Abstract
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Abstract

One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH₂P⁺Ph₃Cl^-, were subsequently treated with Br₂/Et₃N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH₃CN-H₂O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

Key words

N-acylbenzotriazole - homologation - aldehyde - acylation - N-halosuccinimide

References

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