A new method for generation and intramolecular diels-alder reaction of N-acyl and N-alkoxycarbonyl-1-aza-1, 3-butadibnes. A one-pot synthesis of 1, 7, 8, 8a- …

T Uyehara, I Suzuki, Y Yamamoto

Index: Uyehara, Tadao; Suzuki, Ichiro; Yamamoto, Yoshinori Tetrahedron Letters, 1990 , vol. 31, # 26 p. 3753 - 3756

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Citation Number: 30

Abstract

Abstract A one-pot transformation, made up of i) generation of N-trimethylsilylaldimines from α, β-unsaturated aldehyde, ii) exchange of the silyl group by acyl and oxycarbonyl groups, and iii) intramolecular Diels-Alder reaction of the resulting ψ', ω'-unsaturated N-acyl-and a related N-oxycarbonyl-1-aza-1-3-butadienes in boiling xylene, gave 1, 7, 8, 8a-tetrahydro-3 (2H)-indolizinones (5), the 2-oxa derivatives of 5, and 1, 2, 3, 8, 9, 9a-hexahydro-4 (4H)- ...