Synthesis and NMR Characterization of a New Coumarin-7, 8-cyclophosphoramide Derivative

Chinese Journal of Magnetic Resonance ›› 2009, Vol. 26 ›› Issue (3): 301-307.

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Synthesis and NMR Characterization of a New Coumarin-7, 8-cyclophosphoramide Derivative

CHEN Xiao-lan；ZHOU Ya-dong；YUAN Jin-wei；LIU Xiang-qian；
ZHANG Shou-ren；QU Ling-bo；ZHAO Yu-fen

1.Key Laboratory of Chemical Biology and Organic Chemistry, Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China; 2.School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450052, China; 3.Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 10084, China

Received:2008-11-11 Revised:2008-12-01 Online:2009-09-05 Published:2010-01-04
Contact: CHEN Xiao-lan

Abstract

Abstract: The Mannich reaction was used to aminomethylate 7-hydroxycoumarin selectively at the 8-C position. The product, 8-(N-alkylaminomethyl) coumarin, was then coupled with bis-β-chloroethyl dichlorophosphamide to form a novel coumarin-7, 8-cyclophosphoramide derivative via the cyclized reaction. The intermediate and the product were analyzed by NMR spectroscopy. The results confirmed the reaction pathway. The structure of the final product was elucidated by DEPT and 2D NMR techniques including ¹H-¹H COSY, HSQC and HMBC. All ¹H and ¹³C NMR chemical shifts of the title compound were assigned.

Key words: NMR, assignment, 2D NMR, coumarin-7, 8-cyclophosphoramide derivative

CLC Number:

O482.53

CHEN Xiao-lan；ZHOU Ya-dong；YUAN Jin-wei；LIU Xiang-qian；
ZHANG Shou-ren；QU Ling-bo；ZHAO Yu-fen. Synthesis and NMR Characterization of a New Coumarin-7, 8-cyclophosphoramide Derivative[J]. Chinese Journal of Magnetic Resonance, 2009, 26(3): 301-307.

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Synthesis and NMR Characterization of a New Coumarin-7, 8-cyclophosphoramide Derivative

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