Journal
SYNTHESIS-STUTTGART
Volume 50, Issue 13, Pages 2601-2607Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591555
Keywords
copper(I) catalysis; azomethine imines; 1,3-dipolar cycloaddition; vinylidenebisphosphonate; dinitrogen-fused heterocycles; bisphosphonates
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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.
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