Organocatalytic asymmetric [3 + 3] annulation of isatin N,N'-cyclic azomethine imines with enals: Efficient approach to functionalized spiro N-heterocyclic oxindoles
Sign Up to like & getrecommendations! Published in 2020 at "Chinese Chemical Letters"
DOI: 10.1016/j.cclet.2020.06.010
Abstract: Abstract An unprecedented chiral secondary amine-catalyzed [3 + 3] annulation of isatin N,N'-cyclic azomethine imines with α,β-unsaturated aldehydes was developed. This strategy allowed the construction of structurally novel spiro N-heterocyclic oxindole derivatives in good yields (up to… read more here.
Keywords: cyclic azomethine; isatin cyclic; azomethine imines; spiro heterocyclic ... See more keywords
1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one based heterobiaryls
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron"
DOI: 10.1016/j.tet.2018.01.046
Abstract: Abstract π-Deficient ethynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with azomethine imines (2-arylidene-5-oxopyrazolidin-2-ium-1-ides). Both CuI-catalyzed and catalyst-free thermally induced reactions proceeded with high regioselectivity providing 6-hetaryl-5-aryl-2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-ones in moderate to excellent yields.… read more here.
Keywords: ethynyl hetarenes; dihydropyrazolo pyrazol; dipolar cycloaddition; azomethine imines ... See more keywords
Transition Metal-Controlled Divergent Annulations of Azomethine Imines with Iodonium Ylides via C-Centered [1,2]-Rearrangement.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00472
Abstract: Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides via C-centered [1,2]-rearrangement have been developed. The azomethine imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition and in… read more here.
Keywords: azomethine imines; controlled divergent; transition metal; metal controlled ... See more keywords
(4 + 3) Cycloaddition Reaction of Sulfonylphthalide with N,N'-Cyclic Azomethine Imines: Synthesis of Pyrimidinone-Fused Naphthoquinones.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00683
Abstract: A base-mediated [4 + 3] cycloaddition reaction of sulfonylphthalide with N,N'-cyclic azomethine imines to facilely synthesize novel pyrimidinone-fused naphthoquinones is described. The prepared compounds can be readily converted to isoquinoline-1,4-dione derivatives via alkaline methanolysis. Alternatively,… read more here.
Keywords: cyclic azomethine; reaction sulfonylphthalide; sulfonylphthalide cyclic; azomethine imines ... See more keywords
Diastereodivergent Synthesis of Pentacyclic Spiroindolines via a Magnesium(II)-Catalyzed Cascade Reaction of N,N'-Cyclic Azomethine Imines with Indolyl-Substituted Isocyanides.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01085
Abstract: Magnesium(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides are reported herein. The method exhibited a high functional group tolerance and broad substrate scope. A series of anti-pentacyclic spiroindolines containing N,N'-fused heterocycle skeletons were… read more here.
Keywords: azomethine imines; pentacyclic spiroindolines; catalyzed cascade; imines indolyl ... See more keywords
Asymmetric Formal [3 + 2]-Cycloaddition of Azomethine Imines with Azlactones To Synthesize Bicyclic Pyrazolidinones.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b02772
Abstract: An efficient enantioselective formal [3 + 2]-cycloaddition of azomethine imines with azlactones has been realized by using a chiral bifunctional bisguanidinium hemisalt as the catalyst. Optically active bicyclic pyrazolidinone compounds were generated under mild reaction… read more here.
Keywords: formal cycloaddition; imines azlactones; azomethine imines; cycloaddition azomethine ... See more keywords
Brønsted Acid-Catalyzed (4 + 3) Cyclization of N, N'-Cyclic Azomethine Imines with Isatoic Anhydrides.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.8b03604
Abstract: A Brønsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). This reaction represents… read more here.
Keywords: cyclic azomethine; isatoic anhydrides; cyclization; azomethine imines ... See more keywords
A catalyst-free 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines and 3-nitroindoles: an easy access to five-ring-fused tetrahydroisoquinolines
Sign Up to like & getrecommendations! Published in 2017 at "Green Chemistry"
DOI: 10.1039/c6gc02517j
Abstract: We have reported herein a catalyst-free 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines and 3-nitroindoles by which a series of five-ring-fused tetrahydroisoquinolines featuring an indoline scaffold were obtained as single diastereomers in moderate to high yields… read more here.
Keywords: cyclic azomethine; azomethine imines; cycloaddition cyclic; catalyst free ... See more keywords
Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C[double bond, length as m-dash]C bond of indoles.
Sign Up to like & getrecommendations! Published in 2018 at "Chemical communications"
DOI: 10.1039/c7cc09640b
Abstract: Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient… read more here.
Keywords: cyclic azomethine; bond; azomethine imines; highly diastereoselective ... See more keywords
DABCO-mediated [3+3] cycloaddition of azomethine imines with in situ generated nitrile oxides from hydroximoyl chlorides.
Sign Up to like & getrecommendations! Published in 2019 at "Chemical communications"
DOI: 10.1039/c9cc05367k
Abstract: A novel cross 1,3-dipolar cycloaddition between azomethine imines with in situ generated nitrile oxides has been developed. This is the first example of employing a reaction partner containing two heteroatoms in the [3+3] cycloaddition involving… read more here.
Keywords: nitrile oxides; azomethine imines; cycloaddition azomethine; imines situ ... See more keywords
An overview of the reactions involving azomethine imines over half a decade
Sign Up to like & getrecommendations! Published in 2021 at "New Journal of Chemistry"
DOI: 10.1039/d1nj01090e
Abstract: Azomethine imines constitute a versatile class of dipoles that are being increasingly used for the synthesis of biologically relevant heterocycles. This review details the various reactions reported in the literature from 2015–2020 involving acyclic, C,N-cyclic… read more here.
Keywords: reactions involving; half decade; involving azomethine; azomethine imines ... See more keywords