Abstract

Condensation of 1-aminonaphthalene with thiophene-2-carbonyl chloride in 2-propanol furnished N-(1-naphthyl)thiophene-2-carboxamide, the treatment of which with an excess of P₂S₅ in anhydrous pyridine led to the corresponding thioamide. Oxidation of the latter with potassium ferricyanide in an alkaline medium according to the Jacobson method yielded 2-(thien-2-yl)naphtho[1,2-d]thiazole. The latter was introduced into the electrophilic substitution reactions: nitration, bromination, formylation, and acylation. The reactions occur exclusively at the position 5 of the thiophene ring.

中文翻译：

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2-（噻吩-2-基）萘并[1,2-d]噻唑的合成及一些反应

摘要

1-氨基萘与噻吩-2-羰基氯在2-丙醇中的缩合反应，得到N-（1-萘基）噻吩-2-羧酰胺，在无水吡啶中用过量的P ₂ S ₅处理得到相应的硫代酰胺。根据Jacobson方法，在碱性介质中用铁氰化钾氧化后者，得到2-（噻吩-2-基）萘并[1,2- d ]噻唑。后者被引入亲电取代反应中：硝化，溴化，甲酰化和酰化。该反应仅在噻吩环的5位发生。