Citation: Huang Xiaoli, Ren Linjing, Pu Jiazhi, He Chunyang, Yao Qiuli. An Access to the gem-Diamine Derivatives from α-Carbamatemethylphosphonate[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2369-2376. doi: 10.6023/cjoc201702016 shu

An Access to the gem-Diamine Derivatives from α-Carbamatemethylphosphonate

School of Pharmacy, Zunyi Medical University, Zunyi, 563000

Corresponding author: Yao Qiuli, yaoqiuli@zmc.edu.cn
Received Date: 15 February 2017
Revised Date: 4 May 2017
Available Online: 4 September 2017
Fund Project: the Education Department of Guizhou Province 201610661006the Science and Technology Foundation of Guizhou Province [2014]7542the National Natural Science Foundation of China 21462056Project supported by the National Natural Science Foundation of China (No. 21462056), the Science and Technology Foundation of Guizhou Province (No.[2014]7542) and the Education Department of Guizhou Province (No. 201610661006)

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The preparation of gem-diamine derivatives of phosphonates from α-carbamatemethylphosphonates is reported. In our earlier work, the reaction of sulfone with dialkylphosphonate gave α-carbamatemethylphosphonate as the major product. However, gem-diamine derivative of phosphonate was unexpectedly formed as a side product when decreasing the amount of dialkylphosphonate. Although few reports exist on the synthesis of this unique structure, gem-diamine derivatives have shown potential biological activity as an anti-cancer reagent. After optimization, a methodology for the synthesis of gem-diamine derivatives of α-carbamatemethylphosphonate is provided. The reaction of α-carbamatemethylsulfone with α-carbamatemethylphosphonate using LiOH as a base and commercial petroleum ether as solvent provided gem-diamine derivatives in good to excellent yields. This simple protocol runs under very mild conditions, and has a broad substrate scope.
- α-carbamatemethylphosphonate,
- gem-diamine derivatives,
- sulfone
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