Synthesis of 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines via consecutive Arbuzov and aza-Michael reactions and their antitumor activity
Sign Up to like & getrecommendations! Published in 2019 at "Mendeleev Communications"
DOI: 10.1016/j.mencom.2019.11.028
Abstract: 1-(2-Aminoethylsulfonyl)-2-phosphorylpyrrolidines have been synthesized via boron trifluoride-catalyzed Arbuzov reaction of 2-ethoxy-1-(vinylsulfonyl)pyrrolidine with triethyl phosphite followed by aza-Michael reaction of thus obtained 2-phosphoryl-1-(vinylsulfonyl)pyrrolidine with secondary amines. The cytotoxicity of the prepared 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines against M-Hela tumor cell… read more here.
Keywords: consecutive arbuzov; synthesis aminoethylsulfonyl; via consecutive; aza michael ... See more keywords
Adamantyl aziridines via aza-Michael initiated ring closure (aza-MIRC) reaction
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DOI: 10.1016/j.tet.2017.01.006
Abstract: Abstract An efficient one-pot synthesis of functionalized adamantylaziridines by aza-Michael initiated ring closure (aza-MIRC) reaction of 1-aminoadamantane with α-halogenated Michael acceptors is described. The reaction goes through an aza-Michael intermediate that undergoes an intramolecular nucleophilic… read more here.
Keywords: initiated ring; ring closure; aza; reaction ... See more keywords
1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles
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DOI: 10.1016/j.tet.2020.131338
Abstract: Abstract An efficient Zn(OTf)2-catalyzed regioselective C–N bond making reaction between a bunch of aryl/heteroaryl-substituted para-quinone methides as ideal 1,6-acceptors and various aromatic/non-aromatic aza-heterocycles bearing N–H moiety namely carbazoles, pyrazoles, indazole, benzotriazole and saccharin is reported.… read more here.
Keywords: quinone methides; michael addition; para quinone; diarylmethyl substituted ... See more keywords
Domino Imino-Aldol-Aza-Michael and Imino-Aldol-Aza-Michael-Imino-Aldol Reactions: Diastereoselective Synthesis of Highly Functionalized 2,6-Disubstituted Piperidines
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron"
DOI: 10.1016/j.tet.2021.132285
Abstract: Abstract Enolate mediated domino imino-aldol-aza-Michael and domino imino-aldol-aza-Michael-imino-aldol reactions of α-(aryl/alkyl)methylidene-β-diketones with activated N-aryl aldimines (1.0 and 2.0 equiv., respectively) have been developed for the diastereoselective (de >99%) synthesis of two sets of highly functionalized… read more here.
Keywords: imino aldol; michael imino; imino; aza michael ... See more keywords
DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2016.11.125
Abstract: Abstract Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts… read more here.
Keywords: disubstituted triazoles; aryl triazoles; michael addition; aza michael ... See more keywords
Ru(II)-Catalyzed Oxidative Olefination of Benzamides: Switchable Aza-Michael and Aza-Wacker Reaction for Synthesis of Isoindolinones.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c01237
Abstract: Selective tandem oxidative C-H olefination-aza-Michael/aza-Wacker reaction of N-arylbenzamides is achieved by fine-tuning between base and additive to access valuable 3-oxoisoindolinyls and 3-oxoisoindolinylidenes, respectively. Careful optimization and control experiments provides a guiding principle in the design… read more here.
Keywords: aza wacker; wacker reaction; oxidative olefination; aza michael ... See more keywords
N-Heterocyclic Carbene-Catalyzed Aza-Michael-Mannich-Lactamization Cascade for the Enantioselective Synthesis of Pyrazoloquinolin-3-ones.
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DOI: 10.1021/acs.orglett.2c04070
Abstract: The enantioselective synthesis of functionalized pyrazoloquinolin-3-ones via N-heterocyclic carbene-catalyzed cascade reaction of α-bromoenals with 2-aminoaryl N-tosyl hydrazones is reported. The in situ-generated α,β-unsaturated acylazoliums underwent an aza-Michael-Mannich-lactamization sequence to afford the tricyclic products bearing three… read more here.
Keywords: aza michael; enantioselective synthesis; pyrazoloquinolin ones; carbene catalyzed ... See more keywords
Chemoselective Installation of Amine Bonds on Proteins through Aza-Michael Ligation
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DOI: 10.1021/jacs.7b10702
Abstract: Chemical modification of proteins is essential for a variety of important diagnostic and therapeutic applications. Many strategies developed to date lack chemo- and regioselectivity as well as result in non-native linkages that may suffer from… read more here.
Keywords: protein; michael ligation; chemoselective installation; aza michael ... See more keywords
Enzymatic synthesis of unsaturated polyesters: functionalization and reversibility of the aza-Michael addition of pendants
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DOI: 10.1039/c8py01655k
Abstract: Enzymatic synthesis of unsaturated polyesters and the temperature-dependent reversibility of the aza-Michael addition of diethyl amine pendants. read more here.
Keywords: synthesis unsaturated; enzymatic synthesis; aza michael; unsaturated polyesters ... See more keywords
Photo-induced C–H bond activation of N,N′-dialkylethylenediamine upon aza-Michael addition to 1,8-pyrenedione: facile synthesis of fluorescent pyrene derivatives
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DOI: 10.1039/c8qo00183a
Abstract: We discovered a reaction between 1,8-pyrenedione and N,N′-dialkylethylenediamine to form highly fluorescent products, via aza-Michael addition followed by double C–H activation facilitated by visible light. Remarkably, the reaction intermediates and mono C–H bond activation product… read more here.
Keywords: pyrenedione; michael addition; reaction; aza michael ... See more keywords
One pot synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles via tandem C–H olefination/aza-Michael addition
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DOI: 10.1039/c9qo01135h
Abstract: An unprecedented one-pot C–H olefination/aza-Michael addition tandem process has been developed for the synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles and alkenes using a [Cp*RhCl2]2/AgOAc/Me4NOAc catalytic system. A relatively wide range of functional groups are tolerated, and… read more here.
Keywords: olefination aza; pyrrolo phenanthridines; pyrrolo; michael addition ... See more keywords