SYNTHESIS OF TETRAHYDROAZOCINO-1,2-BENZOQUINONES AND DIHYDROAZEPINO-1,2-BENZOQUINONES VIA AMINO-CLAISEN REARRANGEMENT OF 4-(2-VINYL-AZETIDINO AND AZIRIDINO)-1,2-BENZOQUINONES

Authors
VIALLON L REINAUD O CAPDEVIELLE P MAUMY M
Citation
L. Viallon et al., SYNTHESIS OF TETRAHYDROAZOCINO-1,2-BENZOQUINONES AND DIHYDROAZEPINO-1,2-BENZOQUINONES VIA AMINO-CLAISEN REARRANGEMENT OF 4-(2-VINYL-AZETIDINO AND AZIRIDINO)-1,2-BENZOQUINONES, Tetrahedron letters, 36(27), 1995, pp. 4787-4790
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
27
Year of publication
1995
Pages
4787 - 4790
Database
ISI
SICI code
0040-4039(1995)36:27<4787:SOTAD>2.0.ZU;2-B
Abstract
Amino-Claisen rearrangement of 4-(2-vinyl- azetidino or aziridino)-5-m ethoxy-1,2-benzoquinones 3a,b selectively gives rise to the new tetrah ydroazocino - quinone 4a or dihydroazepino - quinone 4b respectively. Based on paramethoxyphenol as starting material, overall yields for th e 3 steps synthesis of heterobicyclic quinones 4a, b are 58 and 52%.