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ABSTRACT:
Synthesis and antibacterial, antitubercular, anticancer, anti AIDS and fungicidal activities of 2-methyl-4-N-2- cyanoethyl-N-methane/benzenesulphonylaminobenzaldehyde and their Hydrazones are reported.
INTRODUCTION:
Tertiary amino benzaldehydes are important due to the role in the synthesis of chemotherapeutics1,2 and analytical reagents 3. Acid hydrazones derived from aldehydes have shown antitubercular4, fungicidal5 activities. The utility of acid hydrazones, we report here synthesis of some titled benzaldehydes and their acid hydrazones which bear 1,3- diketoamino structural feature analogues to pyrimidine bases as potential biomimetics.
m-Toluidine on monocyanoethylation6 in presence of cupric acetate gave N-2-cyanoethyl-mtoluidine. Reaction of the later with the methane sulphonyl chloride or benzene sulphonyl chloride in presence of sodium hydroxide gave two tertiary amines: (1) N-2-cyanoethyl- Nmethanesulphonyl- m-toluidine and (2) N-2-cyanoethyl- Nbenzenesul phonyl-m-toluidine formylation of these two sulphonyl toluidine using DMF/POCl3 gave 2-methyl-4-N- 2- cyanoethyl-N-methanesulphonylaminobenzaldehyde (3) and 2-methyl-4-N-2-cyanoethyl-N-benzenesulphonyl aminobenzaldehyde (4). Condensation of the new aldehydes (3, 4) with malonanilic acid hydrazides7,8 furnished malonanilic acid hydrazones (5a-j, 6a-j) in yield ranging from 55% to 79% (Scheme 1)
Structure of the new products was confirmed by elemental analysis and spectral data
EXPERIMENTAL:
All melting points are uncorrected. The IR spectra were taken on the Perkin Elmer-577 model spectrometer and elemental analysis was carried out by CEST-110 model.
4-N-2-Cyanoethyl-N-methanesulphonyl-m-toluidine
A mixture of 4-N-2-cyanoethyl-m-toluidine (1.5 g, 0.01 mol) and aqueous sodium hydroxide (5 ml, 10%) was heated on boiling water bath methane sulphonyl chloride (3 ml) was added with constant stirring when a solid was obtained as white crystals (73%); m.p. 75 0C; (Found:...