Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solvent ess conditions

Alajos Grün, István Gábor Molnár, Béla Bertók, István Greiner, György Keglevich

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The synthesis of hydroxy-methyl-enebisphosphonates (2a-c) by the addition of dialkyl phosphite to the carbonyl group of the corresponding α-oxophosphonate (1a-c) was studied under microwave irradiation (MW) and solventless conditions in the presence of dialkylamine as the catalyst. After optimization, products 2a and 2b were obtained selectively and in good yields avoiding the formation of the phosphonate-phosphate by-product (3a and 3b) that is the result ofa rearrangement. The MW-assisted synthesis ofhydroxybisphosphonates (2a and 2b) offers complete conversions and a chemoselectivity of 100% as compared to the not so efficient thermal reaction. At the same time, the phenyl-substituted methylenebis-phosphonate 2c could be obtained in only 75% selectivity.

Original languageEnglish
Pages (from-to)350-354
Number of pages5
JournalHeteroatom Chemistry
Volume20
Issue number6
DOIs
Publication statusPublished - Dec 1 2009

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solvent ess conditions'. Together they form a unique fingerprint.

  • Cite this