Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of Para‐Quinone Methides with Thiols

Author:

Zhong Yuan1ORCID,Li Guichen1,Zhang Dan1,Xie Yuxuan1,Hao Long1,Cai Zhengjun2,Wang Xin3

Affiliation:

1. State Key Laboratory of Aridland Crop Science College of Life Science and Technology Gansu Agricultural University Lanzhou 730070 China

2. School of Pharmaceutical Science Sun Yat-Sen University Guangzhou 510006 China

3. School of Pharmacy Lanzhou University Lanzhou 730000 China

Abstract

AbstractPhosphine‐catalyzed chemodivergent reactions of para‐quinone methides (p‐QMs) affording a wide variety of diarylmethyl thioether derivatives have been reported. In the transformation presented in this work, P(4‐FC6H4)3 catalyzed the direct 1,6‐addition of p‐QMs with thiols, whereas P(4‐MeC6H4)3 promoted the tandem addition/self‐aldol condensation reactions of p‐QMs with 1,4‐dithiane‐2,5‐diol. Moreover, some of the obtained products were screened against cancer cell lines HepG2, NB4, and K562, and one was found to inhibit the proliferation of all the tested cancer cell types.

Funder

Natural Science Foundation of Gansu Province

Publisher

Wiley

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