Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN

Muthupandi Nagaraj; Muthusamy Boominathan; Shanmugam Muthusubramanian; Nattamai Bhuvanesh

doi:10.1039/c1ob05232b

Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN

Org Biomol Chem. 2011 Jun 21;9(12):4642-52. doi: 10.1039/c1ob05232b. Epub 2011 Apr 28.

Authors

Muthupandi Nagaraj¹, Muthusamy Boominathan, Shanmugam Muthusubramanian, Nattamai Bhuvanesh

Affiliation

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, 625 021, India.

PMID: 21526255
DOI: 10.1039/c1ob05232b

Abstract

A simple and efficient protocol for the construction of substituted piperazines, piperidines, thiomorpholines, decahydroquinolines, perhydrocyclopenta[b]pyridine, and pyrrolidines bearing N-hydroxy substituents through intramolecular reductive cyclization of diketoximes using sodium cyanoborohydride is described.

Publication types

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

MeSH terms

Borohydrides / chemistry
Chemistry, Pharmaceutical*
Cyclization
Molecular Structure
Morpholines / chemical synthesis*
Oximes / chemistry
Piperazines / chemical synthesis*
Piperidines / chemical synthesis*
Pyridines / chemical synthesis*
Pyrrolidines / chemical synthesis*
Quinolines / chemical synthesis*
Stereoisomerism

Substances

Borohydrides
Morpholines
Oximes
Piperazines
Piperidines
Pyridines
Pyrrolidines
Quinolines
thiamorpholine
decahydroquinoline-5-carboxylic acid
sodium cyanoborohydride