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“Tert-amino effect” in heterocyclic synthesis. Synthesis of thieno[3,2-e]indolizines and thieno[2,3-c]quinolizines

✍ Scribed by W. Verboom; C. Verboom; I. M. Eissink; B. H. M. Lammerink; D. N. Reinhoudt

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 382 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901090907

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✦ Synopsis

Abstract

A new and convenient route for the synthesis of the thieno[3,2‐e]indolizines 4a,b,d, the thieno[2,3‐c]quinolizine 4e and their [1]benzothieno analogues 9a,b is presented. Reaction of the (dialkylamino)thiophenes 1, 5 and 7 with (methoxymethylene)malononitrile (2) gives the Michael adducts 3, 6 and 8. Heating of 3 and 8 in refluxing 1‐butanol gives the cyclized products 4 and 9. This cyclization proceeds via a 1,5 hydrogen shift, followed by an intramolecular addition of the carbanion to the iminium double bond in the intermediate 10 formed. The scope and limitations of this approach are discussed.

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