Synthesis 2019; 51(15): 2923-2935
DOI: 10.1055/s-0037-1611528
paper
© Georg Thieme Verlag Stuttgart · New York

O-Vinylphosphonylated Salicylaldehydes as Aldo-Vinyl Bifunctional Building Blocks for anti-3,4-Disubstituted Phosphadihydrocoumarins

Qinghe Wang
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
,
Dulin Kong
b   School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
,
Tiao Huang
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
,
Mingshu Wu*
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 14 September 2019

Accepted after revision: 02 April 2019

Publication Date:
30 April 2019 (online)


Abstract

An efficient synthetic strategy for anti-3,4-disubstituted phosphadihydrocoumarin compounds has been established by tandem aza-Michael–aldol-like annulations of tetrahydroisoquinolines with O-vinylphosphonylated salicylaldehydes as an aldo-vinyl bifunctional building block. This conversion was characterized by ‘green’ properties such as a step- and atom-economy, catalyst-free conditions, highly anti-selectivity­, and readily available starting materials.

Supporting Information

 
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