Aza-Henry and aza-Knoevenagel reactions of nitriles for the synthesis of pyrido[1,2-a] indoles

N-(Propargyl)indole-2-carbonitriles undergo DBU-catalyzed addition of CH-acids to nitriles, followed by cyclization to give 9-aminopyrido[1,2-a]indoles. The reaction proceeds through the initial formation of a push-pull enamine, alkyne-allene rearrangement and intramolecular nucleophilic cyclization. Nitromethane and malonate esters can be employed as the CH-acids. The resulting compounds were found to exhibit fluorescence properties. © 2020 The Royal Society of Chemistry.

Authors
Zalte R.R. 1 , Festa A.A. 1 , Golantsov N.E. 1 , Subramani K. 1 , Rybakov V.B. 2 , Varlamov A.V. 1 , Luque R. 1, 3 , Luque R. 1, 3 , Voskressensky L.G. 1
Journal
Chemical Communications
Publisher
Royal Society of Chemistry
Number of issue
48
Language
English
Pages
6527-6530
Status
Published
Link
External link
DOI
10.1039/d0cc01652g
Volume
56
Year
2020
Organizations
  • 1 Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya str., Moscow, Russian Federation
  • 2 Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation
  • 3 Departamento de Quimica Organica, Universidad de Cordoba, Campus de Rabanales, Edificio Marie Curie (C-3), Ctra Nnal IV-A, Km 396, Cordoba, Spain
Keywords
Cyanides; Hydrocarbons; Carbonitriles; Enamines; Fluorescence properties; Knoevenagel reaction; Malonates; Nitromethane; Propargyl; Push pull; Cyclization; indole derivative; nitrile; pyrido[1,2 a]indole derivative; unclassified drug; annulation reaction; Article; aza Henry reaction; aza Knoevenagel reaction; biotransformation; chemical analysis; chemical reaction; chemical structure; column chromatography; cyclization; deprotonation; nucleophilicity; ring closing metathesis; stoichiometry; synthesis
Date of creation
02.11.2020
Date of change
02.11.2020
Short link
https://repository.rudn.ru/en/records/article/record/64647/
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