TITLE:
Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones
AUTHORS:
Prasanna K. Vuram, C. Kabilan, Anju Chadha
KEYWORDS:
Catalyst-Free, Isatin, Indole, Microwave, Solvent-Free
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.5 No.2,
June
30,
2015
ABSTRACT: A simple and efficient method for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones using microwave irradiation without catalyst and solvent is described. A series of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones have been synthesized in very short reaction times of 5 and 10 minutes and in yields ranging from 31% to 98% and from 53% to 78% respectively. This method offers a significant advantage over the conventional methods in terms of simplicity and shorter reaction time. To the best of our knowledge compounds N-allyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (6c), N-allyl-3-hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (8c), N-benzyl-3-hydroxy-3-(1-methyl-indol-3-yl) indolin-2-one (10c), N-propargyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (13c), N-propargyl-3-hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (14c), 3-(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (1e), 3-1-methyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (2e), 3-1-allyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (3e), 3-1-benzyl(5-methoxy-1H-in- dol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (4e) and 3-1-(prop-2-ynyl)(5-methoxy-1H-indol-3-yl)-3(1H-indol-3-yl)indolin-2-one (5e) are reported here for the first time. All the compounds are characterized by IR, 1H, 13C NMR and HRMS.