Divergent Approach to Thiazolylidene Derivatives: A Perspective on the Synthesis of a Heterocyclic Skeleton from β-Amidothioamides Reactivity

Stefania Santeusanio; Roberta Majer; Francesca Romana Perrulli; Lucia De Crescentini; Gianfranco Favi; Gianluca Giorgi; Fabio Mantellini

doi:10.1021/acs.joc.7b02135

Divergent Approach to Thiazolylidene Derivatives: A Perspective on the Synthesis of a Heterocyclic Skeleton from β-Amidothioamides Reactivity

J Org Chem. 2017 Sep 15;82(18):9773-9778. doi: 10.1021/acs.joc.7b02135. Epub 2017 Sep 5.

Authors

Stefania Santeusanio¹, Roberta Majer¹, Francesca Romana Perrulli¹, Lucia De Crescentini¹, Gianfranco Favi¹, Gianluca Giorgi², Fabio Mantellini¹

Affiliations

¹ Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo" , Via I Maggetti 24, 61029 Urbino, Italy.
² Department of Chemistry, University of Siena , Via Aldo Moro, 53100 Siena, Italy.

PMID: 28846848
DOI: 10.1021/acs.joc.7b02135

Abstract

Herein we report a domino protocol able to reach regioselectively thiazolylidene systems by combining the reactive peculiarities of both β-amidothioamides (ATAs) and 1,2-diaza-1,3-dienes (DDs). Depending on the reaction conditions and/or the nature of the residue at C4 of the heterodiene system, ATAs can act as hetero-mononucleophiles or hetero-dinucleophiles in the diversified thiazolylidene ring assembly.

Publication types

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