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Synthesis of Oxazolidinones by a Solid‐Phase/Activation Cycloelimination (SP/ACE) Methodology
Author(s) -
ten Holte Peter,
van Esseveldt Bart C. J.,
Thijs Lambertus,
Zwanenburg Binne
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:15<2965::aid-ejoc2965>3.0.co;2-z
Subject(s) - chemistry , isocyanate , alcohol , solid phase synthesis , combinatorial chemistry , diol , sulfonyl , organic chemistry , biochemistry , peptide , alkyl , polyurethane
A versatile method for the solid‐phase synthesis of oxazolidinones is described. An appropriate 1,2‐diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions. The subsequent reaction of the other alcohol group with an isocyanate, followed by a base‐promoted cycloelimination gives an oxazolidinone. By proper choice of isocyanates, functionalities can be introduced which are essential for antibiotic activity.