The palladium-catalyzed reaction of 5-bromo-3-diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (3) with a variety of vinyl-, aryl-, heteroaryl- and alkynylstannanes 4 provides a general and efficient method for the synthesis of 5-substituted isothiazole 1,1-dioxides 5. Different reaction conditions (catalyst, solvent, temperature) were tested for the coupling. The best results were obtained using toluene at reflux and benzylchlorobis(triphenylphosphine)palladium as catalyst. When organostannanes appeared to be less reactive, prolonged heating resulted in the formation of variable amounts of the reduction product-3-diethyiamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (1).

Isothiazoles. Part VII. An efficient palladinm-catalyzed functionalization of 3-amino-4-aryl-isothiazole 1,1-dioxides with organostannanes / F. Clerici, E. Erba, M.L. Gelmi, M. Valle. - In: TETRAHEDRON. - ISSN 0040-4020. - 53:46(1997), pp. 15859-15866.

Isothiazoles. Part VII. An efficient palladinm-catalyzed functionalization of 3-amino-4-aryl-isothiazole 1,1-dioxides with organostannanes

F. Clerici
Primo
;
E. Erba
Secondo
;
M.L. Gelmi
Penultimo
;
1997

Abstract

The palladium-catalyzed reaction of 5-bromo-3-diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (3) with a variety of vinyl-, aryl-, heteroaryl- and alkynylstannanes 4 provides a general and efficient method for the synthesis of 5-substituted isothiazole 1,1-dioxides 5. Different reaction conditions (catalyst, solvent, temperature) were tested for the coupling. The best results were obtained using toluene at reflux and benzylchlorobis(triphenylphosphine)palladium as catalyst. When organostannanes appeared to be less reactive, prolonged heating resulted in the formation of variable amounts of the reduction product-3-diethyiamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (1).
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/181897
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