Rhodium-Catalyzed [4 + 2]-Annulation of o‑Acylanilines with N‑Sulfonyl-1,2,3-triazoles: Synthesis of 3‑Aminoquinolines

Efficient synthesis of 3-aminoquinolines has been demonstrated from readily accessible N-sulfonyl-1,2,3-triazoles and o-acylaniline derivatives. This transformation involves the generation of C–C and C–N bonds through insertion of rhodium azavinyl carbenoid into a N–H bond followed by cyclization and aromatization. The important features include good functional group tolerance, synthesis of indoloquinoline, and isolation of N–H-inserted product, a potential intermediate.

本研究成功实现了以易得的N-磺酰基-1,2,3-三氮唑（N-sulfonyl-1,2,3-triazoles）与邻酰基苯胺衍生物（o-acylaniline derivatives）为原料，高效合成3-氨基喹啉（3-aminoquinolines）的方法。该转化过程通过将铑氮杂乙烯基卡宾体（rhodium azavinyl carbenoid）插入氮氢键（N–H bond），随后经环化（cyclization）与芳构化（aromatization）步骤，生成碳-碳键（C–C bond）与碳-氮键（C–N bond）。该方法的核心特征包括良好的官能团耐受性、可合成吲哚并喹啉（indoloquinoline）类化合物，以及可分离得到作为潜在中间体的氮氢键插入产物（N–H-inserted product）。