REACTION OF STEROID-17-ALPHA-HYDROXY-17-CARBOXYLIC ACIDS WITH CARBODIIMIDES - SYNTHESIS OF STEROID-17-SPIRO-5'-[2'-IMINO-4'-OXAZOLIDINONES]AND 17-SPIRO-5'-[2',4'-OXAZOLIDINEDIONES]

Authors
NOGUCHI S FUJII A HASHITANI K ISHIZU T
Citation
S. Noguchi et al., REACTION OF STEROID-17-ALPHA-HYDROXY-17-CARBOXYLIC ACIDS WITH CARBODIIMIDES - SYNTHESIS OF STEROID-17-SPIRO-5'-[2'-IMINO-4'-OXAZOLIDINONES]AND 17-SPIRO-5'-[2',4'-OXAZOLIDINEDIONES], Chemical and Pharmaceutical Bulletin, 42(8), 1994, pp. 1567-1570
Citations number
17
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
42
Issue
8
Year of publication
1994
Pages
1567 - 1570
Database
ISI
SICI code
0009-2363(1994)42:8<1567:ROSAWC>2.0.ZU;2-Q
Abstract
Steroid-17 alpha-hydroxy-17-carboxylic acids (2) were allowed to react with carbodiimides (DCCI, DPCI, DTCI, EDCI) to afford 17-spiro-5'-[2' -imino-4'-oxazolidinones] (3-5, 11), 17-spiro-5'-[2',4'-oxazolidinedio nes] (77-9) and N-acylureas (10), depending on the reaction conditions . The reaction in acetonitrile in the presence of CuCI2 gave 3-5, whil e that in N,N-dimethylformamide gave 7-9. The reaction with DTCI under basic conditions afforded 10 along with 9.