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11.17.1.4.2 Fragments S—C—N and C—C

DOI: 10.1055/sos-SD-011-00783

Kikelj, D.; Urleb, U.Science of Synthesis, (200211642.

The construction of the thiazole ring from SCN and CC fragments is the most widely used approach to the heterocycle. Here the heteroatoms from aminothiocarbonyl compounds function as nucleophiles, and CC fragments act as electrophiles. The CC fragment is often an α-halocarbonyl compound (Hantzsch synthesis) and the formation of the thiazole ring proceeds via primary S-alkylation,[‌184‌] although some exceptions are described.[‌185‌] The resulting isothiourea, an imidothioate derivative, or its corresponding salt cyclizes easily to the thiazole with concomitant elimination of water. Depending on the reaction conditions, free bases or the corresponding salts are the reaction products. Mostly dry solvents are used (e.g., EtOH, Et2O, DMF, benzene, or 1,4-dioxane).

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