[2,3] SIGMATROPIC REARRANGEMENT OF 1-VINYLIC TETRAHYDROISOQUINOLINE N-YLIDES AND N-OXIDES

Authors
BAILEY TS BREMNER JB CARVER JA
Citation
Ts. Bailey et al., [2,3] SIGMATROPIC REARRANGEMENT OF 1-VINYLIC TETRAHYDROISOQUINOLINE N-YLIDES AND N-OXIDES, Tetrahedron letters, 34(20), 1993, pp. 3331-3334
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
20
Year of publication
1993
Pages
3331 - 3334
Database
ISI
SICI code
0040-4039(1993)34:20<3331:[SRO1T>2.0.ZU;2-8
Abstract
[2.3] Sigmatropic rearrangement of the N-ylides from the 1-vinyl and 1 -(1-propenyl) tetrahydroisoquinolinium salts 3a and 3b at room tempera ture in acetonitrile gave high yields of the functionalised 3-benzazon ine derivatives 6a (90%: E/Z = 19) and 6b (93%: E/Z = 2) respectively. The N-oxide analogues 4a and 4b gave the 2.3-benzoxazepines 8a and 8b , together with the first representative of the 4,3-benzoxazonine syst em, 9b, from 4b.