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2‐Substituted 5‐Acetyl‐4‐Thiazolyl Triflates as Useful Building Blocks for the Preparation of Functionalized Thiazoles
Author(s) -
Arcadi Antonio,
Attanasi Orazio A.,
Guidi Barbara,
Rossi Elisabetta,
Santeusanio Stefania
Publication year - 1999
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/(sici)1099-0690(199911)1999:11<3117::aid-ejoc3117>3.0.co;2-o
Subject(s) - chemistry , deoxygenation , reagent , trifluoromethanesulfonate , annulation , palladium , combinatorial chemistry , organic chemistry , coupling reaction , catalysis , medicinal chemistry
The readily available 2‐substituted 5‐acetyl‐4‐thiazolyl triflates 2 are useful building blocks for the preparation of functionalised thiazoles by means of palladium‐catalysed cross‐coupling reactions with organometallic reagents and alkoxycarbonylation and deoxygenation reactions. The combination of palladium‐catalysed coupling of 2 together with 1‐alkynes/6‐ endo‐dig annulation reactions in the presence of ammonia leads to functionalised pyrido[3,4‐ c ]thiazoles in satisfactory yields. The utilisation of uncatalysed displacement reactions of the triflate group represents a very simple method for the synthesis of 4‐ N ‐,4‐ O ‐, and 4‐ S ‐substituted thiazoles.