A convenient synthesis and biological evaluation of some novel linear and cyclic alpha-aminophosphonic acid derivatives containing a quinazolinone ring

作者：Ali Tarik E^*; El Edfawy Somaya M

来源：Research on Chemical Intermediates, 2016, 42(2): 1329-1347.

DOI：10.1007/s11164-015-2088-0

• alpha-Aminophosphonic acid
• Pudovik reaction
• 1,4,2-Oxazaphosphinanes
• Antimicrobial
• Antioxidant

Synthesis of some novel linear and cyclic alpha-aminophosphonic acids and their esters bearing a quinazolin-4(3H)-one ring was achieved. The methodology depends on Pudovik reaction conditions in which using 3-(benzylideneamino)-2-phenyl-quinazolin-4(3H)-one (2) with phosphorous acid, diethyl phosphite and tris(2-chloroethyl) phosphite gives the corresponding linear alpha-aminophosphonic acid derivatives 3, 5 and 7, respectively, in good yields. Heterocyclization of the linear compounds to 1,4,2-oxazaphosphinanes as cyclic alpha-aminophosphonic acid derivatives 4, 6 and 8, respectively, was carried out. The synthesized compounds were evaluated for their antimicrobial and antioxidant activities. The cyclic alpha-aminophosphonic acids and their esters showed better antimicrobial and antioxidant activities than the corresponding linear alpha-aminophosphonic acids and their esters.

• 出版日期2016-2