A novel versatile strategy for synthesis of new series of thiazolo-triazine <i style="">N</i>-nucleosides

Abstract

An efficient protocol associated with readily available starting materials, mild conditions, excellent yields, and a broad range of products in synthetic chemistry has been established for the synthesis of thiazolo-triazine <i style="">N</i>-nucleosides derivative. Cyclocondensation of <i style="">N</i>-benzylidene-5-phenylthiazol-2-amine <b style="">1a-g</b> and chloromethanamine <b style="">2 </b>on montmorillonite K-10 under microwave irradiation give <b style="">3a-g</b>, which upon nucleophilic substitution with 4-chlorobutanal give <b style="">4a-g</b>. Compounds <b style="">4a-g </b>on control aldol condensation with formaldehyde yield <b style="">5a-g</b>, which on subsequent chemoselective reduction with NaBH₄ give title compounds <b style="">6a-g</b>. Result obtained show considerable enhancement of yields and reduction in time. Furthermore integrated process minimizes the mechanical loss of the intermediate during process for isolation. Coexistence of acidic and basic sites on surface of montmorillonite K-10 accelerates the organic reactions synergistically.