Synthesis of novel 3-phenyl-2-oxido/sulfido-1,3,4,2-benzoxadiazaphosphepines

Abstract

An efficient and facile synthetic approach towards a series of novel 3-phenyl-2-oxido/sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepines 2–7 was described. The method depended on the cyclocondensation of equimolar ratios of salicylaldehyde phenylhydrazone (1) with different examples of phosphorus halides and phosphorus sulfides in toluene containing triethylamine as a catalyst. In the same manner, the fusion of salicylaldehyde phenylhydrazone (1) with triethyl phosphate in the presence of DBU afforded the 2-ethoxy-1,3,4,2-benzoxa-diazaphosphepine 8, while a fusion of compound 1 with diethyl phosphite and tris(2-chloroethyl)phosphite led to the formation of new examples of 1,2-benzoxaphospholes 9 and 10, respectively. Interestingly, the reaction of compound 1 with diethyl ethoxycarbonyl phosphonate in ethanol containing DBU as a catalyst furnished the chromeno[3,4-d][1,2,3]diazaphosphole derivative 12 as a regioselective product.

Graphical Abstract

Keywords:

• 1,3,4,2-Benzoxadiazaphosphepine
• 1,2-benzoxaphosphole
• 1,2,3-diazaphosphole
• salicylaldehyde phenylhydrazone

Additional information

Funding

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through research groups program under grant number R.G.P.1/22/38.