Prins cascade cyclization for the synthesis of 1,9-dioxa-4-azaspiro[5.5]undecane derivatives

B V Subba Reddy; Durgaprasad Medaboina; B Sridhar; Kiran Kumar Singarapu

doi:10.1021/jo4027534

Prins cascade cyclization for the synthesis of 1,9-dioxa-4-azaspiro[5.5]undecane derivatives

J Org Chem. 2014 Mar 7;79(5):2289-95. doi: 10.1021/jo4027534. Epub 2014 Feb 24.

Authors

B V Subba Reddy¹, Durgaprasad Medaboina, B Sridhar, Kiran Kumar Singarapu

Affiliation

¹ Natural Product Chemistry, ‡Laboratory of X-ray Crystallography, and §Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology , Hyderabad-500 007, India.

PMID: 24533744
DOI: 10.1021/jo4027534

Abstract

A novel Prins cascade process for the synthesis of 1,9-dioxa-4- azaspiro[5.5]undecane derivatives by the coupling of aldehydes with N-(4-hydroxy-2-methylenebutyl)-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide has been developed. This is the first report of the synthesis of spiromorpholinotetrahydropyran derivatives through a Prins bicyclization.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Azabicyclo Compounds / chemical synthesis*
Azabicyclo Compounds / chemistry
Cyclization
Molecular Structure
Sulfonamides / chemistry*

Substances

1,9-dioxa-4-azaspiro(5.5)undecane
Aldehydes
Azabicyclo Compounds
N-(4-hydroxy-2-methylenebutyl)-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide
Sulfonamides