ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Chemoselective synthesis of β-enaminones from ynones and aminoalkyl-, phenol- and thioanilines under metal-free conditions

Xue Cui, Yu Chen, Wei Wang, Tingting Zeng, Youbin Li, and Xuesong Wang

Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Provincial Key Laboratory for Research and Development of Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou, People’s Republic of China

E-mail: wxuesong18@163.com

Received: 17 September 2020  Accepted: 9 March 2021

Abstract:

Abstract

An effective strategy for the chemoselective synthesis of β-enaminones is described by aza-Michael addition of aminoalkyl-, phenol- and thio-anilines to ynones under metal-free conditions. Diverse structural β-enaminones were obtained in up to 99% yield for 31 examples. The novel dual-1,5-disubstituted triazole scaffold was synthesized subsequently from β-enaminone. This strategy is highly efficient, highly chemoselective and metal-free.

Graphic Abstract

Keywords: Chemoselective; β-enaminones; Ynones; Amines with two nucleophilic sites; Metal-free

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01599-7

Chemical Papers 75 (7) 3625–3634 (2021)