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

Qinghe Wang; Dulin Kong; Tiao Huang; Mingshu Wu

doi:10.1055/s-0037-1611528

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(15): 2923-2935
DOI: 10.1055/s-0037-1611528

paper

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

Qinghe Wang

^aKey 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

^bSchool of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China eMail: wmsh@hainnu.edu.cn

,

Tiao Huang

^aKey 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*

^aKey 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

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Abstract

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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.

Key words

benzo[e][1,2]oxaphosphinine - β-amino-β′-hydroxyalkylphosphonate - phosphadihydrocoumarin - tetrahydroisoquinoline - intermolecular annulation

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