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Synthesis of α‐hydroxy‐methylenebisphos‐phonates by the microwave‐assisted reaction of α‐oxophosphonates and dialkyl phosphites under solventless conditions

Synthesis of α‐hydroxy‐methylenebisphos‐phonates by the microwave‐assisted reaction of... The synthesis of hydroxy‐methylenebisphosphonates (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 of a rearrangement. The MW‐assisted synthesis of hydroxybisphosphonates (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 methylenebisphosphonate 2c could be obtained in only 75% selectivity. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:350–354, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20558 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Synthesis of α‐hydroxy‐methylenebisphos‐phonates by the microwave‐assisted reaction of α‐oxophosphonates and dialkyl phosphites under solventless conditions

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References (6)

Publisher
Wiley
Copyright
Copyright © 2009 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.20558
Publisher site
See Article on Publisher Site

Abstract

The synthesis of hydroxy‐methylenebisphosphonates (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 of a rearrangement. The MW‐assisted synthesis of hydroxybisphosphonates (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 methylenebisphosphonate 2c could be obtained in only 75% selectivity. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:350–354, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20558

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2009

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