Please use this identifier to cite or link to this item:
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)
Appears in Collections:IJC-B Vol.44B(07) [July 2005]

Files in This Item:
File Description SizeFormat 
IJCB 44B(7) 1470-1475.pdf63.57 kBAdobe PDFView/Open

Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.