Functionalised pyridine sulfolenes as precursors to pyridine o-quinodimethane derivatives and their [4+2] cycloadducts

Authors
Cappelle, SL Vogels, IA Van Meervelt, L Compernolle, F Hoornaert, GJ
Citation
Sl. Cappelle et al., Functionalised pyridine sulfolenes as precursors to pyridine o-quinodimethane derivatives and their [4+2] cycloadducts, TETRAHEDR L, 42(22), 2001, pp. 3759-3762
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
22
Year of publication
2001
Pages
3759 - 3762
Database
ISI
SICI code
0040-4039(20010528)42:22<3759:FPSAPT>2.0.ZU;2-V
Abstract
An efficient route has been developed for the synthesis of polysubstituted 6,6-dioxo-6,7-dihydrothieno[3,4-b]pyridine 5. This pyridine sulfolene compo und serves as an excellent precursor for the corresponding pyridine o-quino dimethane. This reactive species is generated via thermal extrusion of sulf ur dioxide and can be trapped in situ with both electron-rich and electron- deficient dienophiles. (C) 2001 Elsevier Science Ltd. All rights reserved.