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Molecules 2016, 21(3), 333; doi:10.3390/molecules21030333

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

1
Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt
2
Chemistry Department, College of Science, King Saud University, P. O. BOX 2455, Riyadh 11451, Saudi Arabia
3
Chemistry Department, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
5
Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 24 December 2015 / Revised: 23 February 2016 / Accepted: 26 February 2016 / Published: 10 March 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1380 KB, uploaded 10 March 2016]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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