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Solid‐Phase Synthesis of 2‐Amino‐5‐sulfanylthiazoles
Author(s) -
Grimstrup Marie,
Zaragoza Florencio
Publication year - 2002
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(200209)2002:17<2953::aid-ejoc2953>3.0.co;2-5
Subject(s) - chemistry , solid phase synthesis , reagent , sulfur , amino acid , thiourea , aryl , cleavage (geology) , combinatorial chemistry , iodine , organic chemistry , peptide , biochemistry , alkyl , geotechnical engineering , fracture (geology) , engineering
A solid‐phase synthesis that provides easy access to 2‐amino‐5‐sulfanylthiazoles with variable substituents at C‐2, C‐4, and C‐5 has been developed. The key step of this synthesis is a new C ‐sulfanylation of resin‐bound 2‐aminothiazoles by mixtures of various sulfur‐containing building blocks and iodine. The resulting 2‐amino‐5‐sulfanylthiazoles were obtained in high purities and yields after cleavage from the support. This synthesis could also be conducted as a multi‐component reaction, in which treatment of resin‐bound thioureas with mixtures of aryl bromomethyl ketones and sulfanylating reagents yielded 2‐amino‐5‐sulfanylthiazoles directly. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)