17954-06-2Relevant academic research and scientific papers
Facile synthesis and biological evaluation of assorted indolyl-3-amides and esters from a single, stable carbonyl nitrile intermediate
Veale, Clinton G.L.,Edkins, Adrienne L.,De La Mare, Jo-Anne,De Kock, Carmen,Smith, Peter J.,Khanye, Setshaba D.
, p. 1860 - 1864 (2015)
The synthesis of biologically relevant amides and esters is routinely conducted under complex reaction conditions or requires the use of additional catalysts in order to generate sensitive electrophilic species for attack by a nucleophile. Here we present the synthesis of different indolic esters and amides from indolyl-3-carbonyl nitrile, without the requirement of anhydrous reaction conditions or catalysts. Additionally, we screened these compounds for potential in vitro antimalarial and anticancer activity, revealing 1H-indolyl-3-carboxylic acid 3-(indolyl-3-carboxamide)aminobenzyl ester to have moderate activity against both lines.
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles
Vala, Anand,Parmar, Deepa,Rayani, Rahul,Kusurkar, Rakesh,Uttam Kaneriya, Ramakrishna Guduru,Gondaliya, Uday,Parmar, Nirali,Soni, Jigar Y.
, p. 689 - 693 (2022/02/21)
1,4,2-Dioxazol-5-ones are known to undergo decarboxylation under thermal conditions followed by Lossen s rearrangement to give isocyanates. Described herein is the in situ trapping of the isocyanates by indoles to give indole-3-carboxamides in good to exc
Chemoselective Cu-catalyzed synthesis of diverseN-arylindole carboxamides, β-oxo amides andN-arylindole-3-carbonitriles using diaryliodonium salts
Kumar Mehra, Manish,Malik, Monika,Kumar, Bintu,Kumar, Dalip
, p. 1109 - 1114 (2021/02/16)
Chemoselective copper-catalyzed synthesis of diverseN-arylindole-3-carboxamides, β-oxo amides andN-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. DiverseN-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produceN-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones andN-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.
Synthesis of 6-substituted 2-pyrrolyl and indolyl benzoxazoles by intramolecular O-arylation in photostimulated reactions
Vaillard, Victoria A.,Guastavino, Javier F.,Buden, Maria E.,Bardagi, Javier I.,Barolo, Silvia M.,Rossi, Roberto A.
experimental part, p. 1507 - 1519 (2012/03/11)
The synthesis of a series of 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C-O cyclization of anions from 2-pyrrole carboxamides, 2-indole carboxamides, or 3-indole carboxamides has been found to proceed in good to excellent yields (41-100%) in DMSO and liquid ammonia. The pyrrole and indole carboxamides are obtained in good to very good isolated yields by an amidation reaction of different 2-haloanilines with 2-carboxylic acid of pyrrole and 2- or 3-carboxylic acid of indole. To explain the regiochemical outcome of these reactions (C-O arylation vs C-N or C-C arylation), a theoretical analysis was performed using DFT methods and the B3LYP functional.
SELECTIVITY IN CYCLOADDITIONS-IX CYCLOADDITIONS OF NITRILE OXIDES TO INDOLES. REACTIVITY AND REGIOCHEMISTRY
Caramella, P,Corsico, A. Coda,Corsaro, A,Del Monte, D.,Albini, F. Marinone
, p. 173 - 182 (2007/10/02)
Cycloadditions of benzonitrile oxide and mesitonitrile oxide to N-methylindole and indole yield the acid sensitive cycloadducts 1 a-d with high regioselectivity.With N-carbethoxyindole the stable cycloadducts 1 e,f and minor amounts of the regioisomeric 2 e,f are isolated.The electron withdrawing substituent reduces both the regioselectivity and the reactivity of the cycloadditions.Frontier orbital considerations, based on MINDO/3 calculations, allow elucidation of the observed changes in reactivity and regiochemistry.
