Acylphosphonates and their Derivatives

Abstract

Introduction Acylphosphonates Enols, Thioenols and Enamines Related to Acylphosphonates and their Derivatives Imine Derivatives of Acylphosphonates Biological Aspects of Acylphosphonates and Derivatives Acknowledgements

Carbamoylphosphonates part 7. An efficient method for the synthesis of hindered carbamoylphosphonates using 4-nitrophenoxycarbonylphosphonate diesters

“…Triethyl phosphonothiolformate (5b, R = R 0 = Et) reacts with amines via the cleavage of the S-acyl bond, 9 to P-acyl fission, which is the characteristic behavioral pattern of simple acylphosphonate diesters toward nucleophiles. 10 The phosphonate diesters 1 (R 0 = alkyl) can subsequently be dealkylated with bromotrimethylsilane 11 (TMSBr) in chloroform 12 followed by methanolysis to the corresponding N-(cyclo)alkylcarbamoylphosphonic acids CPOs, 1, R 0 = H). As has been pointed out, some CPOs are active as MMP inhibitors, and are potentially useful in the treatment of various diseases such as cancer metastasis, 2,3,13 arthritis, and several other connective tissue-related disorders that have been shown to be mediated by MMPs.…”