SYNTHESIS OF BRIDGED BICYCLIC HYDRAZINES VIA ENDOCYCLIC N-ACYLHYDRAZONIUM INTERMEDIATES - A NOVEL ROUTE TO THE 1-AZATROPANE SKELETON

Authors
RUTJES FPJT HIEMSTRA H PIRRUNG FOH SPECKAMP WN
Citation
Fpjt. Rutjes et al., SYNTHESIS OF BRIDGED BICYCLIC HYDRAZINES VIA ENDOCYCLIC N-ACYLHYDRAZONIUM INTERMEDIATES - A NOVEL ROUTE TO THE 1-AZATROPANE SKELETON, Tetrahedron, 49(44), 1993, pp. 10027-10048
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
44
Year of publication
1993
Pages
10027 - 10048
Database
ISI
SICI code
0040-4020(1993)49:44<10027:SOBBHV>2.0.ZU;2-N
Abstract
Bicyclic molecules with the 1,7-diaza-6,6-dimethylbicyclo[2.2.1]heptan e and 1,8-diaza-7,7-dimethyl-bicyclo[3.2.1]octane (1-aza-7,7-dimethylt ropane) skeleton are shown to be efficiently synthesized via cyclizati on reactions of endocyclic N-acylhydrazonium intermediates. By using a protected beta-ketoester as the internal nucleophile, azacocaine anal ogues are also accessible via this methodology.