CuI-Catalyzed [3+2] Cycloaddition of Hindered Vinylidenebisphosphonates (VBP) with Azomethine Imines for Highly Regioselective Access to Dinitrogen-Heterobicycle-Containing Bisphosphonates

Zhongxiang Zhu; Qinghe Wang; Dulin Kong; Tiao Huang; Mingshu Wu

doi:10.1055/s-0036-1591555

Synthesis, Table of Contents

Synthesis 2018; 50(13): 2601-2607
DOI: 10.1055/s-0036-1591555

paper

CuI-Catalyzed [3+2] Cycloaddition of Hindered Vinylidenebisphosphonates (VBP) with Azomethine Imines for Highly Regioselective Access to Dinitrogen-Heterobicycle-Containing Bisphosphonates

Zhongxiang Zhu

^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 Email: wmsh@hainnu.edu.cn Email: wumingshu@126.com

,

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 Email: wmsh@hainnu.edu.cn Email: wumingshu@126.com

,

Dulin Kong

^bSchool of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China

,

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 Email: wmsh@hainnu.edu.cn Email: wumingshu@126.com

,

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 Email: wmsh@hainnu.edu.cn Email: wumingshu@126.com

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Abstract

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Abstract

A concise, atom-economic, and highly regioselective synthetic strategy for the construction of several dinitrogen-fused heterocycles bearing bisphosphonates by 1,3-dipolar cycloaddition reaction of azomethine imines with tetraethyl vinylidene-1,1-bisphosphonate in the presence of CuI in toluene media has been developed. The targeted compounds were obtained in good yields and with excellent regioselectivity. This method for the synthesis of gem-bisphosphonates (BPs) is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

Key words

copper(I) catalysis - azomethine imines - 1,3-dipolar cycloaddition - vinylidenebisphosphonate - dinitrogen-fused heterocycles - bisphosphonates

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References

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