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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.44B [2005] >
IJC-B Vol.44B(07) [July 2005] >
| Title: | Chemoselective reaction of benz(g)indole based bisheterocycle dicarboxylate towards hydrazine hydrate: Synthesis and antimicrobial activity of new triheterocycles-5-pyrrolylaminocarbonyl/ mercaptooxadiazolyl/4-allyl-5-mercaptotriazolylmethoxy-1-furfuryl-2-methylbenz(g)indoles |
| Authors: | Donawade, Dundappa S
Raghu, A V
Muddapur, U M
Gadaginamath, Guru S |
| Keywords: | Benz (g) indole
bisheterocycle dicarboxylate
hydrazine hydrate
thiosemicarbazide
antibacterial activity
antifungal activity |
| Issue Date: | Jul-2005 |
| Publisher: | CSIR |
| IPC Code: | Int.Cl.7 C 07 D 209/60 // A 61 P 31/04, 31/10 |
| Abstract: | Chemoselectivity of C5-ester over
that of C3-ester function of the benz(g)indole based
bisheterocycle dicarboxylate towards the nucleophilic attack of hydrazine hydrate
has been evidenced by the exclusive formation of 1-furfuryl-3-ethoxycarbonyl-5-hydroxy-2-methylbenz(g)indole-5-yloxyacetic
acid hydrazide 5 which is
reacted separately with acetonyl acetone, carbon disulphide in boiling
ethanolic potassium hydroxide and allyl isothiocyanate to produce respectively 1-furfuryl-3-ethoxycarbonyl-5-(2,5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylbenz(g)indole
7, 1-furfuryl-3-ethoxy-carbonyl-5-(5-mercapto-1,3,4-oxadiazol-2-yl)methoxy-2-methylbenz(g)
indole 8, and 1-furfuryl-3-ethoxycarbonyl-5-(N-allylthiosemicarbazinocarbonyl)methoxy-2-methylbenz(g)indole
9. The thiosemicarbazide 9
when heated with 4% NaOH undergoes cyclisation with concomitant hydrolysis of C3-ester
group to yield 1-fufuryl-5-(4-allyl-5-mercapto-1,2,4-triazol-3-yl)methoxy-2-methylbenz(g)indole-3-carboxylic
acid 10. The structures of newly
synthesized compounds are confirmed on the basis of their spectral and
analytical data and the compounds are also screened for their antibacterial and
antifungal activities. |
| Page(s): | 1470-1475 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.44B(07) [July 2005]
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