A new synthesis of 6-aminonicotinic acid derivatives was developed starting from the readily available 3-substituted acrylamidines 1 and electron-poor alkynes 2. By nucleophilic addition of the basic amidinic NH to the electron-poor triple bond, the intermediate azatrienes 4 were obtained. Through thermally induced electrocyclization compounds 4 afforded the pyridines 3 by alcohol elimination or oxidation. Another approach was the direct cyclization of acrylamidines with the dienyne system as a backbone. (C) 2000 Elsevier Science Ltd.

Isothiazoles. Part 11: 3-Azahexatrienes from 2-arylpropenamidines: Electrocyclization to 6-aminonicotinic acid derivatives / E.M. Beccalli, F. Clerici, M.L. Gelmi. - In: TETRAHEDRON. - ISSN 0040-4020. - 56:27(2000), pp. 4817-4821.

Isothiazoles. Part 11: 3-Azahexatrienes from 2-arylpropenamidines: Electrocyclization to 6-aminonicotinic acid derivatives

E.M. Beccalli
Primo
;
F. Clerici
Secondo
;
M.L. Gelmi
Ultimo
2000

Abstract

A new synthesis of 6-aminonicotinic acid derivatives was developed starting from the readily available 3-substituted acrylamidines 1 and electron-poor alkynes 2. By nucleophilic addition of the basic amidinic NH to the electron-poor triple bond, the intermediate azatrienes 4 were obtained. Through thermally induced electrocyclization compounds 4 afforded the pyridines 3 by alcohol elimination or oxidation. Another approach was the direct cyclization of acrylamidines with the dienyne system as a backbone. (C) 2000 Elsevier Science Ltd.
Amidines; Electrocyclic reactions; Isothiazoles; Pyridines
Settore CHIM/06 - Chimica Organica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/181823
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