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Preferential intramolecular ring closure of aminoalcohols with diethyl carbonate to oxazolidinones

Authors :
Fumiko Fujisaki
Marumi Oishi
Kunihiro Sumoto
Source :
Chemicalpharmaceutical bulletin. 55(5)
Publication Year :
2007

Abstract

The closure by cyclization with diethyl carbonate (EtO)(2)CO from aminoalcohols 1 as starting material can lead to the oxazolidinones 2a, b and 2c, respectively. In the reaction of trans-isomer (6) and (EtO)(2)CO, isolated products were also only 5-membered oxazolidinone derivative (7), containing its dehydrated derivative 8. The preferential formation of the 5-membered oxazolidinone ring system apparently indicated that this process (5-Exo-Trig ring closure) is more favorable than that of 6- or 7-membered ring derivative (3 or 9) by 6- or 7-Exo-Trig ring closure.

Details

ISSN :
00092363
Volume :
55
Issue :
5
Database :
OpenAIRE
Journal :
Chemicalpharmaceutical bulletin
Accession number :
edsair.doi.dedup.....d96dc7795e6a74592e78cad0fd29f1b3