Author
Karamil Jayaprakash
Bio: Karamil Jayaprakash is an academic researcher from Indian Institute of Technology Madras. The author has contributed to research in topics: One-pot synthesis & Aryl. The author has an hindex of 1, co-authored 2 publications receiving 17 citations.
Topics: One-pot synthesis, Aryl, Yield (chemistry)
Papers
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TL;DR: In this paper, N -propargylanilines, under one-pot homologation conditions, undergo an in situ cyclisation catalysed by Cu(I) to yield 3-pyrrolines in good yield.
18 citations
TL;DR: In this paper, N -propargylanilines, under one-pot homologation conditions, undergo an in situ cyclisation catalysed by Cu(I) to yield 3-pyrrolines in good yield.
Abstract: N -propargylanilines, under one-pot homologation conditions, undergo an in situ cyclisation catalysed by Cu(I) to yield 3-pyrrolines in good yield.
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TL;DR: The different synthetic approaches to synthesize propargylamines, such as A3 couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses.
Abstract: Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A3 couplings and C–H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.
298 citations
TL;DR: In this article, Palladium-catalyzed cyclization of α-amino allenes affords either the pyrroline or pyrrole depending on reaction conditions and provides for introduction of an aryl substituent at the C-3 position of the α-amerino allene.
90 citations
TL;DR: 1,1-carboboration is favoured as a result of the increased steric hindrance (1,3-allylic strain) in the 5-alkylidene-4,5-dihydrooxazolium borate species.
Abstract: A series of propargyl amides were prepared and their reactions with the Lewis acidic compound B(C6F5)3 were investigated. These reactions were shown to afford novel heterocycles under mild conditions. The reaction of a variety of N-substituted propargyl amides with B(C6F5)3 led to an intramolecular oxo-boration cyclisation reaction, which afforded the 5-alkylidene-4,5-dihydrooxazolium borate species. Secondary propargyl amides gave oxazoles in B(C6F5)3 mediated (catalytic) cyclisation reactions. In the special case of disubstitution adjacent to the nitrogen atom, 1,1-carboboration is favoured as a result of the increased steric hindrance (1,3-allylic strain) in the 5-alkylidene-4,5-dihydrooxazolium borate species.
65 citations
TL;DR: The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes.
Abstract: Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates to afford scalemic α-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes.
40 citations
TL;DR: The allylation of aminocoumarins in the presence of excess of anhydrous K(2)CO(3) and allyl bromide to diallylaminocOUmarins is described and most of them were found to be potent lipid peroxidation inhibitors in vitro.
37 citations