Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P.R. China.
Org Biomol Chem. 2019 Aug 7;17(29):6994-6997. doi: 10.1039/c9ob01098j. Epub 2019 Jul 12.
A highly efficient cascade bicyclization reaction of o-alkenylphenyl isothiocyanates with propargylamines has been developed, which affords a series of thiazolo[2,3-b]quinazolines in good to excellent yields by using KCO as a base in MeCN at 80 °C. This method is transition-metal-free and operationally simple with broad functional group tolerance. Mechanistically, 6-exo-trig hydroamination followed by 5-exo-dig hydrothiolation was involved in this transformation.
一种高效的邻烯基苯异硫氰酸酯与炔丙胺的级联双环化反应已经被开发出来，该反应在 80°C 的 MeCN 中以 KCO3 作为碱，可以得到一系列噻唑并[2,3-b]喹唑啉，产率良好至优秀。该方法无需过渡金属，操作简单，具有广泛的官能团容忍性。在机理上，该转化涉及 6-endo-trig 氨化反应和 5-exo-dig 硫氢化反应。
