A concise access to 6-azabicyclo[3.1.0] hexanes via high-pressure promotedcycloaddition reaction of azides to ABH

Authors
Ishikura, M Kudo, S Hino, A Ohnuki, N Katagiri, N
Citation
M. Ishikura et al., A concise access to 6-azabicyclo[3.1.0] hexanes via high-pressure promotedcycloaddition reaction of azides to ABH, HETEROCYCLE, 53(7), 2000, pp. 1499-1504
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
7
Year of publication
2000
Pages
1499 - 1504
Database
ISI
SICI code
0385-5414(20000701)53:7<1499:ACAT6H>2.0.ZU;2-5
Abstract
Cycloaddition reaction of electron-deficient azides (5a, b) to 2-azabicyclo [2.2.1]hept-5-en-3-one (ABH) (1) was accelerated by high-pressure, leading to a mixture of regioisomeric triazolines (6) in good yields. Then, 6 were in turn, through photolysis and ring opening sequences, converted to 6-azab icyclo[3.1.0]-hexanes (8).