A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis

Efficient syntheses are described for the synthetically important 3-methylquinoline-4-carbaldehydes 6a–h from o-nitrobenzaldehydes 1a–h employing a Wittig-olefination–Claisen-rearrangement protocol. The Wittig reaction of o-nitrobenzaldehydes with crotyloxymethylene triphenylphosphorane afforded cro...

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Main Authors:	Mukund G. Kulkarni, Mayur P. Desai, Deekshaputra R. Birhade, Yunus B. Shaikh, Ajit N. Dhatrak, Ramesh Gannimani
Format:	Article
Language:	English
Published:	Beilstein-Institut 2012-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	acetal Claisen rearrangement oxidative cleavage ring-closure Wittig olefination
Online Access:	https://doi.org/10.3762/bjoc.8.197

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spelling	doaj-3198da7c50514e78838a56a03039ce182021-02-02T05:48:23ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-10-01811725172910.3762/bjoc.8.1971860-5397-8-197A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesisMukund G. Kulkarni0Mayur P. Desai1Deekshaputra R. Birhade2Yunus B. Shaikh3Ajit N. Dhatrak4Ramesh Gannimani5Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007, India; Fax: +91 (020) 25691728Efficient syntheses are described for the synthetically important 3-methylquinoline-4-carbaldehydes 6a–h from o-nitrobenzaldehydes 1a–h employing a Wittig-olefination–Claisen-rearrangement protocol. The Wittig reaction of o-nitrobenzaldehydes with crotyloxymethylene triphenylphosphorane afforded crotyl vinyl ethers 2a–h, which on heating under reflux in xylene underwent Claisen rearrangement to give 4-pentenals 3a–h. Protection of the aldehyde group of the 4-pentenals as acetals 4a–h and subsequent oxidative cleavage of the terminal olefin furnished nitroaldehydes 5a–h. Reductive cyclization of these nitroaldehydes yielded the required 3-methylquinoline-4-carbaldehydes 6a–h in excellent yields. Therefore, an efficient method was developed for the preparation of 3-methylquinoline-4-carbaldehydes from o-nitrobenzaldehydes in a simple five-step procedure.https://doi.org/10.3762/bjoc.8.197acetalClaisen rearrangementoxidative cleavagering-closureWittig olefination
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Mukund G. Kulkarni Mayur P. Desai Deekshaputra R. Birhade Yunus B. Shaikh Ajit N. Dhatrak Ramesh Gannimani
spellingShingle	Mukund G. Kulkarni Mayur P. Desai Deekshaputra R. Birhade Yunus B. Shaikh Ajit N. Dhatrak Ramesh Gannimani A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis Beilstein Journal of Organic Chemistry acetal Claisen rearrangement oxidative cleavage ring-closure Wittig olefination
author_facet	Mukund G. Kulkarni Mayur P. Desai Deekshaputra R. Birhade Yunus B. Shaikh Ajit N. Dhatrak Ramesh Gannimani
author_sort	Mukund G. Kulkarni
title	A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
title_short	A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
title_full	A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
title_fullStr	A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
title_full_unstemmed	A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
title_sort	wittig-olefination–claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2012-10-01
description	Efficient syntheses are described for the synthetically important 3-methylquinoline-4-carbaldehydes 6a–h from o-nitrobenzaldehydes 1a–h employing a Wittig-olefination–Claisen-rearrangement protocol. The Wittig reaction of o-nitrobenzaldehydes with crotyloxymethylene triphenylphosphorane afforded crotyl vinyl ethers 2a–h, which on heating under reflux in xylene underwent Claisen rearrangement to give 4-pentenals 3a–h. Protection of the aldehyde group of the 4-pentenals as acetals 4a–h and subsequent oxidative cleavage of the terminal olefin furnished nitroaldehydes 5a–h. Reductive cyclization of these nitroaldehydes yielded the required 3-methylquinoline-4-carbaldehydes 6a–h in excellent yields. Therefore, an efficient method was developed for the preparation of 3-methylquinoline-4-carbaldehydes from o-nitrobenzaldehydes in a simple five-step procedure.
topic	acetal Claisen rearrangement oxidative cleavage ring-closure Wittig olefination
url	https://doi.org/10.3762/bjoc.8.197
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A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis

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