The synthesis of a new series of six-membered N,N’-diarylsubstituted methylene-bis-dthydro-2H-1,3-benzoxazines (5a-e) was achieved in excellent yields by Mannich-type condensation of N,N’-diarylsubstiuted methyiene-bis-o-hydroxybenzyl amines (4a- e) with formaldehyde in chioroform at reflux.These amines (4a-e) were obtained by the reduction of N,N’-diarylsubstituted methylene-bis-o-hydroxybenzyl imines (3a-e) with NaBH_4,which inturn were obtained by the condensation of methylene-bis- salicylaldehyde (2) with various substituted arylamines. The synthesis of a new series of six-membered N, N’-diarylsubstituted methylene-bis-dthydro-2H-1,3-benzoxazines (5a-e) was achieved in excellent yields by Mannich-type condensation of N, The diarylsubstiuted methyiene-bis-o-hydroxybenzyl amines (4a-e) with formaldehyde in chioroform at reflux.The amines (4a-e) were obtained by the reduction of N, N’-diarylsubstituted methylene-bis- -e) with NaBH_4, which inturn were obtained by the condensation of methylene-bis- salicylaldehyde (2) with various substituted arylamines.