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Dimerization of Phenylalanine: An Approach to Thiazoles and Oxazoles Involved S/O‐Insertion
Author(s) -
Cheng Yan,
Xiang JiaChen,
Wang ZiXuan,
Ma JinTian,
Wang Miao,
Tang BoCheng,
Wu YanDong,
Zhu YanPing,
Wu AnXin
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701130
Subject(s) - chemistry , deamination , decarboxylation , heteroatom , phenylalanine , ring (chemistry) , amino acid , oligomer , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , enzyme
We herein describe the development of a dimerization procedure for amino acids to prepare 2,5‐disubstituted thiazoles and oxazoles in the presence of Na 2 S⋅9H 2 O and H 2 O, respectively. These approaches enabled the direct formation of five‐membered ring systems bearing two different heteroatoms from two amino acid units. Mechanically, decarboxylation, deamination, S/O insertion, cyclization and gradient oxidation processes were involved in the oligomer formation.