A one-pot synthesis of bis(phenylimino)thiazolidines from ketene N,S-acetals and [Formula: see text],[Formula: see text]-diphenyloxalimidoyl dichloride

Issa Yavari; Nooshin Zahedi; Leila Baoosi; Stavroula Skoulika

doi:10.1007/s11030-017-9783-2

A one-pot synthesis of bis(phenylimino)thiazolidines from ketene N,S-acetals and [Formula: see text],[Formula: see text]-diphenyloxalimidoyl dichloride

Mol Divers. 2018 Feb;22(1):11-19. doi: 10.1007/s11030-017-9783-2. Epub 2017 Sep 21.

Authors

Issa Yavari¹, Nooshin Zahedi², Leila Baoosi², Stavroula Skoulika³

Affiliations

¹ Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran. yavarisa@modares.ac.ir.
² Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran.
³ Laboratory of Physical Chemistry, Department of Chemistry, The University of Ioannina, 45110, Ioannina, Greece.

PMID: 28936770
DOI: 10.1007/s11030-017-9783-2

Abstract

A synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-ylidenes via a simple reaction between ketene [Formula: see text]-acetals (derived from isothiocyanates and acetonitrile derivatives) with N,[Formula: see text]-diphenyloxalimidoyl dichloride in the presence of KOH in DMF is described. When CS[Formula: see text] was used as the heterocumulene component, the reaction led to the formation of 4,5-bis(phenylimino)-1,3-dithiolan-2-ylidene derivatives, in moderate to good yields.

Keywords: Heterocyclic synthesis; Ketene acetals; Push–pull olefins; Thiazolidine.

MeSH terms

Acetals / chemistry*
Chemistry Techniques, Synthetic*
Ethylenes / chemistry*
Ketones / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Thiazolidines / chemical synthesis*

Substances

Acetals
Ethylenes
Ketones
Thiazolidines
ketene