APPLICATION OF THE MITSUNOBU REACTION IN THE MORPHINE SERIES .121. THE REACTION OF 14-BETA-CHLORO AND 14-BETA-BROMOCODEINE WITH PHTHALIMIDEAND DIPHENYLPHOSPHORYL AZIDE

Authors
SIMON C HOSZTAFI S MAKLEIT S
Citation
C. Simon et al., APPLICATION OF THE MITSUNOBU REACTION IN THE MORPHINE SERIES .121. THE REACTION OF 14-BETA-CHLORO AND 14-BETA-BROMOCODEINE WITH PHTHALIMIDEAND DIPHENYLPHOSPHORYL AZIDE, Tetrahedron letters, 34(40), 1993, pp. 6475-6478
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
40
Year of publication
1993
Pages
6475 - 6478
Database
ISI
SICI code
0040-4039(1993)34:40<6475:AOTMRI>2.0.ZU;2-U
Abstract
14beta-Chlorocodeme 1 reacted with phthalimide under the conditions of the Mitsunobu reaction (with TPP and DEAD or DIAD ) to give the expec ted phthalimide derivative 3 together with 6beta,14beta-dichloro-6-deo xycodeine 4 and the diene 6 or 7. 14beta-Bromocodeine 2 reacted simila rly but did not give any phthalimido derivative. The mechanism of thes e consecutive reactions has been investigated. With diphenylphosphoryl azide 6beta-azido-14beta-chloro 15 and 6beta-azido-14beta-bromo 16 de rivatives were obtained.