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
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron"
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
Sign Up to like & getrecommendations! Published in 2020 at "Tetrahedron"
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.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
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
A Concise Enantioselective Synthesis of Fluorinated Pyrazolo-Piperidine GSK3901383A Enabled by an Organocatalytic Aza-Michael Addition.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.3c03694
Abstract: A highly enantioselective organocatalytic aza-Michael addition of 4-nitro-pyrazole to ethyl (E)-2,2-difluoro-5-oxopent-3-enoate has been developed. This reaction enabled a concise, four-step, stereoselective synthesis of highly functionalized 3,3-difluoro-4-pyrazolo-piperidine GSK3901383A, a key intermediate for the synthesis of a… read more here.
Keywords: pyrazolo piperidine; piperidine gsk3901383a; organocatalytic aza; michael addition ... See more keywords
N-Benzyloxyacrylamides as Bisnucleophiles in an Organocatalyzed Domino aza-Michael/Morita-Baylis-Hillman Sequence.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.4c00295
Abstract: We herein describe a stereoselective organocatalyzed aza-Michael/Morita-Baylis-Hillman domino reaction between readily accessible acrylamides and α,β-unsaturated carbonyls. This novel, PPh3-promoted atom economic one-pot process features medium to good yields and good stereoselectivity leading to variously substituted… read more here.
Keywords: baylis hillman; aza michael; michael morita; morita baylis ... See more keywords
Energetic Nitrate-Based Polymer-Bonded Explosives Derived from Sustainable Aza-Michael Reactions
Sign Up to like & getrecommendations! Published in 2024 at "ACS Omega"
DOI: 10.1021/acsomega.4c00349
Abstract: A novel nontoxic method for processing energetic binder, namely, polyglycidyl nitrate (PGN), using Aza-Michael reactions for deriving high-performance explosive formulations is being reported. The polyol binders used in polymer-bonded explosives (PBX) including PGN are usually… read more here.
Keywords: nitrate; michael reactions; aza michael; polymer bonded ... See more keywords
Deciphering the Microdroplet Acceleration Factors of Aza-Michael Addition Reactions.
Sign Up to like & getrecommendations! Published in 2024 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c02312
Abstract: Microdroplet chemistry is emerging as a great tool for accelerating reactions by several orders of magnitude. Several unique properties such as extreme pHs, interfacial electric fields (IEFs), and partial solvation have been reported to be… read more here.
Keywords: chemistry; michael addition; aza michael; microdroplet acceleration ... See more keywords