Synlett 2003(7): 0971-0974
DOI: 10.1055/s-2003-39306
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Diels-Alder Reactions of 4-Alkoxy-4-alkylcyclohexa-2,5-dienimines: Synthesis of 5-Alkylindoles

Peter V. Zawada, Scott C. Banfield, Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7 Canada
e-Mail: makerr@uwo.ca;
Further Information

Publication History

Received 2 April 2003
Publication Date:
20 May 2003 (online)

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Abstract

N-arylsulfonyl 4-alkoxy-4-alkylcyclohexadienimines undergo thermal Diels-Alder reactions with 1,3-butadienes to yield the expected cycloadducts. The crude adducts when treated with anhydrous acid yield dihydronaphthalenes which when subjected to a series of simple transformations produce 5-alkyl indoles in good overall yields.