Benzo[d][1,3]Oxazine‐Assisted C─H Annulation of Arenes with Diarylacetylenes: Access to 3,4‐diarylisoquinolinones
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DOI: 10.1002/ajoc.202500225
Abstract: A novel Rh(III)‐catalyzed [4 + 2] annulation of diarylacetylenes with 2‐aryl‐4H‐benzo[d][1,3]oxazines is described to produce a new class of 3,4‐diarylisoquinolinones through a ring‐opening C─H annulation of benzo[d][1,3]oxazine moiety. This is the first report on C─H functionalazation of… read more here.
Keywords: annulation; oxazine assisted; benzo oxazine; assisted annulation ... See more keywords
A Direct Synthesis of 3‐Acylanthranils via A One‐Pot Oxidation and Electrophilic‐Halogen‐Induced Annulation from 2‐Alkynylanilines
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DOI: 10.1002/ajoc.202500366
Abstract: The current study features the development of a new method to convert 2‐alkynylanilines to 3‐acylanthranils which have served as a valuable retron for 2‐aminobenzaldehyde derivatives and as building blocks in conversion to other tremendously useful… read more here.
Keywords: annulation; direct synthesis; synthesis acylanthranils; pot ... See more keywords
Non‐Noble Metal Catalysis in Focus: Unlocking Latest Emergent Frontiers in Amide Annulation Through C─H/C─X Activation
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DOI: 10.1002/ajoc.202500478
Abstract: The non‐noble metal‐catalyzed annulation of amide molecules through the proximal C─H/C─X (X = halogens, O, S, N, C etc.) has emerged as a transformative approach in contemporary synthetic chemistry, enabling the efficient construction of diverse heterocyclic frameworks.… read more here.
Keywords: annulation; chemistry; non noble; activation ... See more keywords
Rh(III)-Catalyzed Redox-Neutral [4+2] Annulation for Direct Assembly of 3-Acyl Isoquinolin-1(2H)-ones as Potent Antitumor Agents.
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DOI: 10.1002/cplu.201900616
Abstract: By virtue of an efficient rhodium(III)-catalyzed redox-neutral C-H activation/ring-opening of a strained ring/[4+2] annulation cascade of N-methoxybenzamides with propargyl cycloalkanols, diverse 3-acyl isoquinolin-1(2H)-ones were directly obtained in good yields and with excellent functional group compatibility.… read more here.
Keywords: annulation; iii catalyzed; redox neutral; isoquinolin ones ... See more keywords
Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
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DOI: 10.1002/ejoc.201601305
Abstract: Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction conditions. The generality of the… read more here.
Keywords: annulation; acceptor cyclopropanes; lewis acid; donor acceptor ... See more keywords
Visible‐Light Induced and PIFA Enabled [4+2] Annulation of Alkenes with N‐Aryl Substituted Hydroxamic Acids
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DOI: 10.1002/ejoc.202400683
Abstract: In this paper, we reported a facial approach for the preparation of benzo[c][1,2]oxazine scaffolds via visible light induced phenyl iodine bis(trifluoroacetate) (PIFA) oxidative [4+2] annulation of vinyl benzenes with N‐aryl substituted hydroxamic acids. In the… read more here.
Keywords: annulation; hydroxamic acids; visible light; aryl substituted ... See more keywords
Additive‐free and Diastereoselective Synthesis for trans‐Disubstituted‐2,3‐dihydro‐benzofurans via [4 + 1] Annulation between p‐QMs and TFISYs
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DOI: 10.1002/ejoc.202400946
Abstract: An additive‐free and diastereoselective [4 + 1] annulation between ortho‐hydroxyphenyl‐substituted para‐quinone methides and CF3‐substituted imidoyl sulfoxonium ylides is developed, providing a facile and practical route to diverse trans‐2,3‐dihydrobenzofurans with high efficiency. This protocol features mild… read more here.
Keywords: annulation; diastereoselective synthesis; synthesis trans; trans disubstituted ... See more keywords
Base‐Mediated Diastereoselective Aza/Oxa‐Michael Approach to Spiro‐Pyrazolone and Spiro‐Oxindole Derivatives Through [4 + 2] Spiro‐Annulation
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DOI: 10.1002/ejoc.202500881
Abstract: A metal‐free, base‐catalyzed double Michael diastereoselective [4 + 2] annulation reaction of para‐quinone methides with alkylidene pyrazolones and isatin‐derived N‐Boc ketimines or isatylidine malonitriles has been developed, leading to biologically inspired spiro‐heterocyclic derivatives under mild reaction conditions… read more here.
Keywords: michael; base mediated; annulation; diastereoselective aza ... See more keywords
Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
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DOI: 10.1016/j.isci.2020.100840
Abstract: Summary A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization–aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiophenes with high optical… read more here.
Keywords: annulation; concise synthesis; synthesis chiral; enantioselective annulation ... See more keywords
Two Catalytic Annulation Modes via Cu-Allenylidenes with Sulfur Ylides that Are Dominated by the Presence or Absence of Trifluoromethyl Substituents
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DOI: 10.1016/j.isci.2020.100994
Abstract: Summary We disclose the Cu-catalyzed enantioselective synthesis of 3-methyl-3-propargyl-indolines, which contain a quaternary stereogenic carbon center, via the decarboxylative [4 + 1] annulation of 4-methyl-4-propargyl-benzoxazinanones with variety of sulfur ylides. The reaction proceeds predominantly through… read more here.
Keywords: annulation; allenylidene intermediates; sulfur ylides; attack allenylidene ... See more keywords
Cerium(IV) based oxidative free radical cyclization of active methylene compounds with some cyclic alkenes: A useful annulation method for terpene functionalization
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DOI: 10.1016/j.tet.2019.03.039
Abstract: Abstract Ceric ammonium nitrate-mediated oxidative cyclizations of CH-acids with terpenes and terpene like substrates were investigated. Dimedone, acetylacetone, and methyl nitroacetate were condensed with pinene, norbornene, nopol, camphene, and carvone and the reaction stereoselectivity was… read more here.
Keywords: free radical; radical cyclization; annulation; cerium based ... See more keywords