G. S. Gadaginamath, A. Shyadligeri
Aug 1, 2000
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Journal
ChemInform
Abstract
Diethyl 5,5' -dihydroxy-2,2' -dimethyl-I ,.1' -( ethaneI ,2-diyl)di( I H-indole)-3,3' -dicarboxylate 3 has been prepared in one-flask procedure by the condensation of diethyl 3,3' -( ethane-2,2' -diyldiimino )butenoate I with I A-benzoqui none 2 in 1:2 molar ratio. Reaction of 3 separately with methyliodide and ethyl chloroacctate afford s the corresponding O-alkylated derivatives 4 and 5. respcctively. Exclusive fo rmation of diethyl 5,5' -bi -(hydrazi nocarbonylmethoxy)-2,2 ' -dimethylI.I '(ethane-I ,2-diyl)di{ IH-indole)-3 ,3'-dicarboxylatc 6 from 5 reveals the chemose lectivity of 5,S'-cster function towards nucleophilic attack of hY9razine hydrate. This di carbohydrazidc 6 on reacting with acetonylacetone furnishes diethyl S.5'bis(2,5-dimethylpyrroll -ylamino-carbonylmclhoxy)-2,2' -dimethyl-I. I' -(cthaneI ,2-diyl)di( lll-indo le)-3 .3'-dicarboxylatc 8. Conformations of all these bisindole derivatives have been established. Compounds 3, 4, 5, 6 and 8 have also been screened for their antibacterial and antifungal activities.