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Action of Hydrazines on 2‐(2‐Oxindolin‐3‐ylidene)malononitrile, ( E , Z )‐Ethyl 2‐cyano‐2‐(2‐oxindolin‐3‐ylidene)acetate and Isatin‐β‐thiosemicarbazone as a Source of Spiro Indoline‐pyrazole Systems
Author(s) -
Youssef Ahmed S. A.,
Hemdan Magdy M.,
Emara Samir A.,
Kamel Rabaa M.
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2163
Subject(s) - chemistry , malononitrile , hydrazine (antidepressant) , isatin , hydrazone , ethyl acetoacetate , semicarbazone , hydrate , medicinal chemistry , pyridine , moiety , acetic anhydride , isophorone , organic chemistry , proton nmr , catalysis , chromatography
2‐(2‐Oxindolin‐3‐ylidene)malononitrile ( 1a ) or ( E , Z )‐ethyl 2‐cyano‐2‐(2‐oxindolin‐3‐ylidene)acetate ( 1b ) or isatin‐β‐thiosemicarbazone ( 1c ) undergoes reactions with prototype hydrazine hydrate itself and some of its simple congeners to give hydrazone derivatives bearing indoline‐2‐one moiety ( 2 ). The hydrazone derivatives ( 2 ) when heated with acetyl acetone or ethyl acetoacetate in dry pyridine afforded the spiro indoline derivatives ( 3a , 3b ). Also, cinnoline derivative ( 9 ) is obtained by action of hydrazine hydrate on the N ‐acetyl derivative of ( 6a ). The structures of the newly synthesized compounds were evaluated by IR, 1 H‐NMR spectroscopy, mass spectra and elemental analyses.