Sterically controlled regiospecific heterocyclization of 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole to 10-methyl-1,2,4-triazolo[4',3':2,3[1,2,4-triazino[5,6-b]indoles.
3-Hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole underwent sterically controlled regiospecific heterocyclizations with a variety of one-carbon cyclizing agents to give the sterically more favored linearly annulated 10-methyl-1,2,4-triazolo[4',3':2,3[1,2,4-triazino[5,6-b]indoles rather than the sterically less favored angularly annulated 10-methyl-1,2,4-triazolo[3',4':3,4]1,2,4-triazino[5,6-b]indoles. The assigned structures were corroborated by comparison with unequivocally synthesized authentics, chemical and spectral data. The antimicrobial activity of some of the prepared compounds was investigated.
Shaban
M A
MA
Department of Chemistry, Faculty of Science, University of Alexandria, Egypt.
Nasr
A Z
AZ
Morgaan
A E
AE
D002176:Candida albicans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006834:Hydrazines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects; D014227:Triazines / Q000737:chemistry*
C404724:3-hydrazino-5-methyl-1,2,4-triazino(5,6-b)indole; D006834:Hydrazines; D007211:Indoles; D014227:Triazines