Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules

Rohit Kumar Varshnaya; Prabal Banerjee

doi:10.1039/C7OB00941K

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Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules†

Rohit Kumar Varshnaya^a and Prabal Banerjee

*^a

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^a Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab-140001, India
E-mail: prabal@iitrpr.ac.in
Web: http://www.iitrpr.ac.in/chemistry/prabal
Fax: +911881223395

Abstract

Lewis acid catalyzed [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with in situ generated mercaptoaldehyde for the synthesis of functionalized thiazine and oxathiane derivatives has been developed. Additionally, this method facilitates the derivatization of thiazines by detosylation and Krapcho monodecarboxylation.

This article is part of the themed collection: Celebrating the RAOBC symposium

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DOI: https://doi.org/10.1039/C7OB00941K
Article type: Paper
Submitted: 17 Agd 2017
Accepted: 30 Cax 2017
First published: 31 Cax 2017

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Org. Biomol. Chem., 2017,15, 5182-5190

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Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules

R. K. Varshnaya and P. Banerjee, Org. Biomol. Chem., 2017, 15, 5182 DOI: 10.1039/C7OB00941K

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Organic & Biomolecular Chemistry

Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules†

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Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules

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