Tetrahedron

Synthesis of new amidino-substituted 2-aminothiophenoles: mild basic ring opening of benzothiazole

L Racané, V Tralić-Kulenović, Z Mihalić, G Pavlović…

Index: Racane, Livio; Tralic-Kulenovic, Vesna; Mihalic, Zlatko; Pavlovic, Gordana; Karminski-Zamola, Grace Tetrahedron, 2008 , vol. 64, # 51 p. 11594 - 11602

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Citation Number: 16

Abstract

The efficient synthesis of new amidino, N-isopropylamidino, 2-imidazolinyl substituted benzothiazoles and 2-aminothiophenoles by the Pinner reaction is described. The novel ring opening of benzothiazole with ammonia and ethylenediamine was found, and a plausible reaction mechanism proposed. The ring opening with ethylenediamine is selective and applicable to compounds bearing hydrolytically and amonolytically unstable ...