Synthesis, Structure, and Reactivity of Naphtho-Fused 2-(Furan-2-yl)-1,3-thiazole


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Аннотация

The condensation of naphthalen-2-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(naphthalen-2-yl)furan-2-carboxamide which was treated with excess P2S5 in anhydrous toluene to obtain the corresponding thioamide. The oxidation of the latter with potassium hexacyanoferrate(III) in alkaline medium afforded 2-(furan-2-yl)naphtho[2,1-d][1,3]thiazole. A probable mechanism of its formation was proposed, and the ring closure involving C1 of the naphthalene fragment was substantiated by quantum chemical calculations. Electrophilic substitution reactions of 2-(furan-2-yl)naphtho[2,1-d][1,3]thiazole (nitration, bromination, formylation, and acylation) involved exclusively the 5-position of the furan ring.

Авторлар туралы

A. Aleksandrov

Platov South-Russian State Polytechnic University

Хат алмасуға жауапты Автор.
Email: aaanet1@yandex.ru
Ресей, ul. Prosveshcheniya 132, Novocherkassk, 346428

M. El’chaninov

Platov South-Russian State Polytechnic University

Email: aaanet1@yandex.ru
Ресей, ul. Prosveshcheniya 132, Novocherkassk, 346428

V. Stepanov

Platov South-Russian State Polytechnic University

Email: aaanet1@yandex.ru
Ресей, ul. Prosveshcheniya 132, Novocherkassk, 346428

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