REACTIONS OF 3,5-DICHLOROSALICYLALDEHYDE WITH ACYLGLYCINE DERIVATIVESAND CERTAIN ENAMINES

Reactions of 3,5-dichlorosalicyladehyde with acylglycine derivatives a fforded exclusively acylaminocoumarins I(a,b) with no apparent formati on of azlactones II. Ring opening of I(a,b) with a variety of amines y ielded the arylcarboxamides III(a-h). On the other hand, I(a) reacts w ith o-phenylenediamine or its 4,5-dimethyl derivative, affording 2-sub stituted benzimidazoles IV(a,b). Furthermore, the reaction of 3,5-dich lorosalicyladehyde with certain enamines produced the corresponding 2- dialkylamino-3-substituted-2H-chromenes V(a-f).