Condition-Dependent Selective Synthesis of Indolo[1,2-<i>c</i>]quinazolines and Indolo[3,2-<i>c</i>]quinolines from 2-(1<i>H</i>-Indol-2-yl)anilines and Sulfoxonium Ylides
Guang Chen, Xinyuan Cai, Xinying Zhang, Xuesen Fan
Abstract
In this paper, a selective synthesis of indolo[1,2-c]quinazolines and indolo[3,2-c]quinolines through the cascade reactions of 2-(1H-indol-2-yl)anilines with sulfoxonium ylides is presented. The formation of products involves the generation of a carbene species from sulfoxonium ylide and its N–H bond insertion reaction with 2-(1H-indol-2-yl)aniline followed by deoxygenative imine formation, intramolecular N– or C– nucleophilic addition and deoxygenative aromatization. This switchable synthesis was condition-dependent. In the presence of K2CO3 in CH3CN, the reaction mainly furnished indolo[1,2-c]quinazolines. In the presence of HOAc in dioxane, it selectively afforded indolo[3,2-c]quinolines. In addition, direct C–H/N–H functionalization of the products obtained provides a convenient and direct access to polycyclic heteroaromatic compounds. These novel protocols have advantages such as readily accessible substrates, easily tunable selectivity, good compatibility with diverse functional groups, and the use of air as a cost-free and sustainable oxidant.