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Synthesis of some heterocyclic compounds based on (2, 3-dioxo-2, 3- dihydro-1H-indol-1-yl) acetyl acetic acid derivatives
International Journal of Basic and Applied Sciences2 • 2013
Publication Information
Authors
M. M. H. Arief 1 , M. H. M. Ahmed 1 , A. A. Said 2 , N. M. M. Selim
Keywords
Isatin, thionyl chloride, chloro acetic acid, hydrazine hydrate, acetic anhydride, ammonium thiocyanate, anthranilic acid, glycine,
benzoyl glycine and benzaldehyde.
Journal
International Journal of Basic and Applied Sciences2
Publisher
Science Publishing Corporation
Volume
2
Issue
2
Pages
153-159
publication.type
International
Paper Link
Not Available
Supplementary Materials
Not Available
Abstract
Reactions of isatin–N–acetylchloride 2 with equivalent amount of hydrazine hydrate gave 2-(2, 3-dioxo-2, 3-dihydro-
1H-indol-1-yl) acetohydrazide 3 which was then cyclized to give [1, 2, 4] triazino [4, 3-a] indole-3, 10 (2H, 4H)-dione 5
but when 2 reacted with excess of hydrazine hydrate it give 2[(2, 3-bishydrazono)-2, 3-dihydro-1H-indol-1-yl]
acetohydrazide 4. Isothiocyanate derivative 6 was prepared from the corresponding acid chloride and ammonium
thiocyanate in acetone. The reactions of isothiocyanate with anthranilic acid, glycine, benzoyl glycine, hydrazine
hydrate and benzoyl hydrazine were also investigated. The condensation reaction of benzoyl glycine with
isothiocyanate in the presence of benzaldehyde gave 16 which was easily cyclized to give 17
1H-indol-1-yl) acetohydrazide 3 which was then cyclized to give [1, 2, 4] triazino [4, 3-a] indole-3, 10 (2H, 4H)-dione 5
but when 2 reacted with excess of hydrazine hydrate it give 2[(2, 3-bishydrazono)-2, 3-dihydro-1H-indol-1-yl]
acetohydrazide 4. Isothiocyanate derivative 6 was prepared from the corresponding acid chloride and ammonium
thiocyanate in acetone. The reactions of isothiocyanate with anthranilic acid, glycine, benzoyl glycine, hydrazine
hydrate and benzoyl hydrazine were also investigated. The condensation reaction of benzoyl glycine with
isothiocyanate in the presence of benzaldehyde gave 16 which was easily cyclized to give 17