Novel unsymmetrical bisindoles were synthesized by a solvent-free C-C bond-formation reaction under mild conditions. Starting from aziridines or hydroxyl precursors, indoles have been used as C-nucleophiles to form new pharmacologically interesting bisindoles via an electrophilic aromatic substitution pathway in good to excellent yields. [reaction: see text]
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http://dx.doi.org/10.1021/ol062338p | DOI Listing |
Org Biomol Chem
February 2024
School of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology (TIET), Patiala-147004, Punjab, India.
Trisindoles are of tremendous interest due to their wide range of biological activities. In this context, a number of methods have been reported in the past to synthesize 3,3',3''-trisindoles. However, most of the methods are only able to produce symmetrical 3,3',3''-trisindoles.
View Article and Find Full Text PDFChem Biodivers
August 2022
Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, 116, Taiwan, R.O.C.
The synthesis of unsymmetrical urea generally requires toxic reagent, solvent and harsh reaction condition. Herein, we introduce Cu-catalyzed greener and safer unsymmetrical urea derivatives synthesis in ethyl acetate. This method minimized utilization of toxic reagent.
View Article and Find Full Text PDFJ Org Chem
June 2020
Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.
The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2'-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3' position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.
View Article and Find Full Text PDFOrg Biomol Chem
April 2019
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600 036, India.
Zn(OTf)2-catalyzed synthesis of 3,3'-bisindolyl acetamides from α-keto amides is developed. Both aromatic α-keto amides substituted with electron-donating as well as -withdrawing groups and aliphatic α-keto amides are well tolerated to provide symmetrical bisindoles in moderate to excellent yields. The chemoselective bisindolylation of the keto group of α-keto amides in the presence of a simple keto functionality is successfully achieved in good yields.
View Article and Find Full Text PDFOrg Lett
August 2017
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
A catalyst-free water-mediated regio- and stereospecific ring-opening reaction of nonracemic spiroaziridine oxindoles and indoles has been developed with retention of configuration. This method provides direct access to enantiopure 3,3'-mixed bisindoles with excellent yield and enantioselectivity (up to 98% ee).
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