A novel synthesis of 2,3-dihydro-1H-thieno[3,4-b]pyrroles via ring transformation of cyclic sulfonium ylides by titanium(IV) chloride-triethylamine system

A series of cyclic sulfonium ylides 4a‐h reacted with titanium(IV) chloride in the presence of triethyl‐amine to give the corresponding fused 2,3‐dihydro‐1H‐thieno[3,4‐b]pyrroles 5a‐h, via a ring opening and recyclization. In contrast, treatment of compounds 4a, 4b, 4e and 4f with titanium(IV) chlor...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2005-05, Vol.42 (4), p.717-721
Main Authors: Maruoka, Hiroshi, Yamagata, Kenji, Okabe, Fumi, Tomioka, Yukihiko
Format: Article
Language:English
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Summary:A series of cyclic sulfonium ylides 4a‐h reacted with titanium(IV) chloride in the presence of triethyl‐amine to give the corresponding fused 2,3‐dihydro‐1H‐thieno[3,4‐b]pyrroles 5a‐h, via a ring opening and recyclization. In contrast, treatment of compounds 4a, 4b, 4e and 4f with titanium(IV) chloride, triethy‐lamine and dimethylamine hydrochloride gave the corresponding thiophenes 6a, 6b, 6e and 6f. Furthermore, compounds 6a and 6b easily underwent cyclization with sodium hydride to afford the corresponding 5a and 5b.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570420438