THERMAL AND PHOTOCHEMICAL-REACTION OF 1-ACETYLINDOLE-2,3-DIONE WITH PYRAZOLONE

Citation
Kc. Joshi et al., THERMAL AND PHOTOCHEMICAL-REACTION OF 1-ACETYLINDOLE-2,3-DIONE WITH PYRAZOLONE, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 33(5), 1994, pp. 483-485
Citations number
13
Language
INGLESE
art.tipo
Note
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0376-4699
Volume
33
Issue
5
Year of publication
1994
Pages
483 - 485
Database
ISI
SICI code
0376-4699(1994)33:5<483:TAPO1W>2.0.ZU;2-Y
Abstract
The reaction of 1-acetylindole-2,3-dione (1a) and 1-acetyl-5-fluoroind ole-2,3-dione (Ib) with pyrazolone (II) has been reported under both t hermal and photochemical conditions. Under thermal conditions Ia react s with II in refluxing ethanol or THF to give yl-5'-oxo-1'-phenyl-4-py razolidene]indol-2(3H)-one (IIIa, 45%) and xo-3-methyl-1-phenyl-10H-py razolo[3,4-b]benzazpine (IV, 17%). However, Ib reacts with 11 to give spiroindoline 1-acetyl-5-fluoro-3', 5'-dimethyl-1', 7-diphenylspiro[in doline-3, 4'-dipyrazolo[3, 4-b; 4', 3'-e]pyran]-2-one (V, 80%). Under photochemical conditions la reacts with 11 in THF yields the same prod ucts IIIa and IV but their yields are 17 and 40% respectively. he comp ound lb on photochemical irradiation with II affords 1-acetyl-5-fluoro -343'-methyl-5'- oxo-1'-phenyl-4'-pyrazolidene]indol-2(3H)-one (IIIb) and 1-acetyl-5-fluoro-3-[2'-(1''-carboxy-2''- oxoethyl)-4'-fluoropheny l]-2H-indol-2-one (VI) in 14 and 37% yields, respectively.