Aqueous-Phase One-Pot Synthesis of 2-Aminothiazole- or 2-Aminoselenazole-5-carboxylates from β-Keto Esters, Thiourea or Selenourea, and N-Bromo-succinimide under Supramolecular Catalysis
Mendu Narender, Majjigapu Somi Reddy, Vydyula Pavan Kumar, Boga Srinivas, Regati Sridhar, Yadavalli Venkata Durga Nageswar, Kakulapati Rama Rao*
*Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: drkrraoyahoo.com
M. Narender, M. S. Reddy, V. P. Kumar, B. Srinivas, R. Sridhar, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2007, 3469-3472.
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2-Amino-4-alkyl- and 2-amino-4-arylthiazole-5-carboxylates and their selenazole analogues were synthesized by α-halogenation of β-keto esters with N-bromosuccinimide, followed by cyclization with thiourea or selenourea, respectively, in the presence of β-cyclodextrin in water at 50°C.
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thiazoles, selenazoles, β-keto esters, N-bromosuccinimide, cyclodextrins