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

W. Verboom*, C. Verboom, I.M. Eissink, B.H.M. Lammerink, D.N. Reinhoudt

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    16 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)481-484
    Number of pages4
    JournalRecueil des Travaux Chimiques des Pays‐Bas
    Volume109
    Issue number9
    DOIs
    Publication statusPublished - 1990

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