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Synthesis of New Functionalized Indoles Based on Ethyl Indol-2-carboxylate

Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt
Chemistry Department, College of Science, King Saud University, P. O. BOX 2455, Riyadh 11451, Saudi Arabia
Chemistry Department, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Roman Dembinski
Molecules 2016, 21(3), 333;
Received: 24 December 2015 / Revised: 23 February 2016 / Accepted: 26 February 2016 / Published: 10 March 2016
(This article belongs to the Section Organic Chemistry)
PDF [1380 KB, uploaded 10 March 2016]


Successful alkylations of the nitrogen of ethyl indol-2-carboxylate were carried out using aq. KOH in acetone. The respective N-alkylated acids could be obtained without separating the N-alkylated esters by increasing the amount of KOH and water. The use of NaOMe in methanol led to transesterification instead of the alkylation, while the use of NaOEt led to low yields of the N-alkylated acids. Hydrazinolysis of the ester gave indol-2-carbohydrazide which then was allowed to react with different aromatic aldehydes and ketones in ethanol catalyzed by acetic acid. Indol-2-thiosemicarbazide was used in a heterocyclization reaction to form thiazoles. The new structures were confirmed using NMR, mass spectrometry and X-ray single crystal analysis. View Full-Text
Keywords: ethyl indol-2-carboxylate; alkylation; hydrazinolysis; single-crystal X-ray diffraction ethyl indol-2-carboxylate; alkylation; hydrazinolysis; single-crystal X-ray diffraction

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Boraei, A.T.A.; El Ashry, E.S.H.; Barakat, A.; Ghabbour, H.A. Synthesis of New Functionalized Indoles Based on Ethyl Indol-2-carboxylate. Molecules 2016, 21, 333.

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