Synlett 2012; 23(20): 2947-2950
DOI: 10.1055/s-0032-1317621
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Highly Functionalized 1,3-Oxathioles via an Unusual [4+1] Annulation of α,α'-Dioxothione with 1,2-Diaza-1,3-dienes

Orazio A. Attanasi*
a   Dipartimento di Scienze della Terra, della Vita e dell’Ambiente (DiSTeVA), Sezione di Chimica Organica e delle Sostanze Organiche Naturali (SCOSON), Università degli Studi di Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino (PU), Italy   Fax: +39(722)3033441   Email: orazio.attanasi@uniurb.it
,
Gianfranco Favi
a   Dipartimento di Scienze della Terra, della Vita e dell’Ambiente (DiSTeVA), Sezione di Chimica Organica e delle Sostanze Organiche Naturali (SCOSON), Università degli Studi di Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino (PU), Italy   Fax: +39(722)3033441   Email: orazio.attanasi@uniurb.it
,
Fabio Mantellini
a   Dipartimento di Scienze della Terra, della Vita e dell’Ambiente (DiSTeVA), Sezione di Chimica Organica e delle Sostanze Organiche Naturali (SCOSON), Università degli Studi di Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino (PU), Italy   Fax: +39(722)3033441   Email: orazio.attanasi@uniurb.it
,
Stefano Menichetti*
b   Dipartimento di Chimica ‘Ugo Schiff’ Polo Scientifico e Tecnologico, Università di Firenze, Via della Lastruccia 3-13, 50019 Sesto Fiorentino, Italy
,
Giada Moscatelli
a   Dipartimento di Scienze della Terra, della Vita e dell’Ambiente (DiSTeVA), Sezione di Chimica Organica e delle Sostanze Organiche Naturali (SCOSON), Università degli Studi di Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino (PU), Italy   Fax: +39(722)3033441   Email: orazio.attanasi@uniurb.it
,
Caterina Viglianisi
b   Dipartimento di Chimica ‘Ugo Schiff’ Polo Scientifico e Tecnologico, Università di Firenze, Via della Lastruccia 3-13, 50019 Sesto Fiorentino, Italy
› Author Affiliations
Further Information

Publication History

Received: 15.10.20120

Accepted: 23 October 2012

Publication Date:
16 November 2012 (online)


Abstract

The present method provides highly functionalized 1,3-oxathioles through an unusual base-promoted [4+1] annulation between α,α'-dioxothione, generated in situ from a phthalimide precursor, and 1,2-diaza-1,3-dienes. An intriguing scaffold comprised of spiro-fused oxathiole and pyrazolone components was also obtained in moderate yield.

 
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