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
The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron"
DOI: 10.1016/j.tet.2018.07.040
Abstract: Abstract The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same… read more here.
Keywords: cyclic azomethine; cyclic nitrones; nitrones cyclic; vinylpyrroles cyclic ... See more keywords
(3 + 2) Cycloaddition Reaction of the Endocyclic N-Silyl Enamine and N,N'-Cyclic Azomethine Imine.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00366
Abstract: We describe the (3 + 2) cycloaddition reaction of endocyclic N-silyl enamines and N,N'-cyclic azomethine imines. This process utilized the versatile endocyclic N-silyl enamine intermediates from the dearomative hydrosilylation of N-heteroarenes. The resulting tetracyclic pyrazolidinone… read more here.
Keywords: silyl enamine; reaction endocyclic; endocyclic silyl; cyclic azomethine ... See more keywords
Chiral-Boron-Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of 2'-Hydroxychalcones with N,N'-Cyclic Azomethine Imines.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02597
Abstract: We report the (R)-3,3'-I2-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of 2'-hydroxychalcones with N,N'-cyclic azomethine imines, providing the corresponding N,N'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >99:1… read more here.
Keywords: catalyzed asymmetric; cycloaddition hydroxychalcones; complex catalyzed; boron complex ... 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
Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N-Cyclic Azomethine Imines.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00984
Abstract: A novel α,β-regioselective [3+2] cycloaddition reaction of arylallene with C,N-cyclic azomethine imine is reported. The axial-to-central chirality transfer phenomenon has been disclosed with chiral allenes in the reaction. The wide substrate scope, including different functional… read more here.
Keywords: cycloaddition chiral; cycloaddition; stereospecific cycloaddition; cyclic azomethine ... 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
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
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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
Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones
Sign Up to like & getrecommendations! Published in 2020 at "New Journal of Chemistry"
DOI: 10.1039/d0nj00887g
Abstract: The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2–5 min. The dicyclic spiropyrrolidine oxoindole… read more here.
Keywords: cyclic azomethine; isatin cyclic; azomethine imine; imine dipoles ... See more keywords