Synthesis of N-(4-bromo-2-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-dialkyl-alpha-aminophosphonates under ultrasonic irradiation

Bao-An Song; Guo-Ping Zhang; Song Yang; De-Yu Hu; Lin-Hong Jin

doi:10.1016/j.ultsonch.2005.03.003

Synthesis of N-(4-bromo-2-trifluoromethylphenyl)-1-(2-fluorophenyl)-O,O-dialkyl-alpha-aminophosphonates under ultrasonic irradiation

Ultrason Sonochem. 2006 Feb;13(2):139-42. doi: 10.1016/j.ultsonch.2005.03.003. Epub 2005 Jun 2.

Authors

Bao-An Song¹, Guo-Ping Zhang, Song Yang, De-Yu Hu, Lin-Hong Jin

Affiliation

¹ Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China. songbaoan22@yahoo.com

PMID: 15936238
DOI: 10.1016/j.ultsonch.2005.03.003

Abstract

Boron trifluoride diethyl etherate catalyzes the Mannich-type reaction of 2-trifluoromethyl-4-bromoaniline and O,O-dialkylphosphite with 2-fluorobenzoaldehyde under ultrasonic irradiation to synthesize the corresponding product alpha-aminophosphonate. The advantages of the procedure include short reaction period, high yield and simple working up. Their structures were clearly established by IR, (1)H NMR, (13)C NMR and elemental analysis. The bioassay tests showed that the title compounds exhibit moderate antitumor activity in vitro by MTT method.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Models, Chemical
Molecular Structure
Organophosphonates / chemical synthesis*
Organophosphonates / pharmacology
Ultrasonics*

Substances

Antineoplastic Agents
Organophosphonates