Synthesis of substituted 3,9-diazaspiro[5.5]undecanes via spirocyclization of pyridine substrates

Sharavathi G Parameswarappa; F.C Pigge

doi:10.1016/j.tetlet.2011.06.055

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Synthesis of substituted 3,9-diazaspiro[5.5]undecanes via spirocyclization of pyridine substrates

Journal article

Peer reviewed

Synthesis of substituted 3,9-diazaspiro[5.5]undecanes via spirocyclization of pyridine substrates

Sharavathi G Parameswarappa and F.C Pigge

Tetrahedron letters, Vol.52(33), pp.4357-4359

08/17/2011

DOI: 10.1016/j.tetlet.2011.06.055

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Abstract

Construction of 3,9-diazaspiro[5.5]undecane derivatives can be easily achieved via intramolecular spirocyclization of 4-substituted pyridines. The reaction entails in situ activation of the pyridine ring with ethyl chloroformate followed by intramolecular addition of an attached β-dicarbonyl nucleophile in the presence of Ti(OiPr)4.

Dearomatization

Pyridine

Spiropiperidine

Spirocyclization

Details

Title: Subtitle: Synthesis of substituted 3,9-diazaspiro[5.5]undecanes via spirocyclization of pyridine substrates
Creators: Sharavathi G Parameswarappa
F.C Pigge
Resource Type: Journal article
Publication Details: Tetrahedron letters, Vol.52(33), pp.4357-4359
Publisher: Elsevier Ltd
DOI: 10.1016/j.tetlet.2011.06.055
ISSN: 0040-4039
eISSN: 1873-3581
Language: English
Date published: 08/17/2011
Academic Unit: Chemistry; Radiology
Record Identifier: 9983985809202771

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