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.

2-substituted 5-acetyl-4-thiazolyl triflates as useful building blocks for the preparation of functionalized thiazoles / A. Arcadi, O. Attanasi, B. Guidi, E. Rossi, S. Santeusanio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :11(1999), pp. 3117-3126.

2-substituted 5-acetyl-4-thiazolyl triflates as useful building blocks for the preparation of functionalized thiazoles

E. Rossi;
1999

Abstract

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.
Heterocycles; Palladium; Pyrido[3,4-c]thiazoles; Thiazoles; Triflates
Settore CHIM/06 - Chimica Organica
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/183972
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