Synthesis of quinolines via sequential addition and I2-mediated desulfurative cyclization

Mingming Yang; Yajun Jian; Weiqiang Zhang; Huaming Sun; Guofang Zhang; Yanyan Wang; Ziwei Gao

doi:10.1039/d1ra06976d

Synthesis of quinolines via sequential addition and I₂-mediated desulfurative cyclization

RSC Adv. 2021 Dec 6;11(61):38889-38893. doi: 10.1039/d1ra06976d. eCollection 2021 Nov 29.

Authors

Mingming Yang¹, Yajun Jian¹, Weiqiang Zhang¹, Huaming Sun¹, Guofang Zhang¹, Yanyan Wang¹, Ziwei Gao^{1

2}

Affiliations

¹ Key Laboratory of Applied Surface and Colloid Chemistry, Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University Xi'an 710119 P. R. China [email protected] [email protected].
² A School of Chemistry & Chemical Engineering, Xinjiang Normal University Urumqi 830054 P. R. China.

Abstract

An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed-a two-step Michael addition-cyclization condensation step leading to intermediate 1,5-benzothiazepine catalyzed by zirconocene amino acid complex Cp₂Zr(η¹-C₉H₁₀NO₂)₂, followed by I₂-mediated desulfurative step.