[4+3]-Cycloaddition Reaction of Sulfilimines with Cyclobutenones: Access to Benzazepinones.

A catalyst-free [4+3]-cycloaddition reaction of N-aryl sulfilimines with cyclobutenones is described, which provides a straightforward protocol for synthesizing 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions. This reaction features a broad substrate scope and good functional group tolerance and does not require catalysts or additives. Moreover, using N-pyridinyl sulfilimine as the substrate, a series of pyridoazepinones have also been prepared.

[1]  I. Alabugin,et al.  Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor-Acceptor Cyclopropanes. , 2021, Journal of the American Chemical Society.

[2]  Guangbin Dong,et al.  Modular Entry to Functionalized Tetrahydrobenzo[b]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene. , 2021, Journal of the American Chemical Society.

[3]  S. Zard,et al.  Modular Approach to Substituted Pyridoazepinones. , 2021, Organic letters.

[4]  Rong Zeng,et al.  Construction of a Benzo[b]azepine Skeleton through Decarboxylative Ylide [6+1] Annulations with Modified Vinyl Benzoxazinanones. , 2021, Organic letters.

[5]  Jianliang Yu,et al.  Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids. , 2020, Angewandte Chemie.

[6]  Chao Ning,et al.  Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives. , 2020, Organic letters.

[7]  Xiaoming Feng,et al.  Asymmetric Catalytic Diverse Ring Opening/Cycloadditions of Cyclobutenones with (E)-Alkenyloxindoles and (E)-Dioxopyrrolidines. , 2020, Organic letters.

[8]  Andrew M. Piggott,et al.  Biosynthesis of a New Benzazepine Alkaloid Nanangelenin A from Aspergillus nanangensis Involves an Unusual L-Kynurenine-Incorporating NRPS Catalyzing Regioselective Lactamization. , 2020, Journal of the American Chemical Society.

[9]  A. Hashmi,et al.  Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C−H Aminations , 2020, Angewandte Chemie.

[10]  D. Wink,et al.  Oxidation of Non-Activated Anilines to Generate N-Aryl Nitrenoids. , 2020, Journal of the American Chemical Society.

[11]  A. Studer,et al.  Reaction of Vinylaziridines with Arynes: Synthesis of Benzazepines and Branched Allyl Fluorides. , 2020, Chemistry.

[12]  P. Lu,et al.  Enantioselective Synthesis of 3-Substituted Cyclobutenes via Catalytic Conjugate Addition/Trapping Strategies. , 2019, Angewandte Chemie.

[13]  A. Hashmi,et al.  α‐Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity , 2019, Chemistry.

[14]  H. Yun,et al.  Asymmetric Synthesis of 1-Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization. , 2019, Organic letters.

[15]  Kan Wang,et al.  Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes. , 2019, Angewandte Chemie.

[16]  O. García Mancheño,et al.  Mild, Metal-Free Oxidative Ring-Expansion Approach for the Synthesis of Benzo[ b]azepines. , 2019, Organic letters.

[17]  Linxing Zhang,et al.  Rhodium-Catalyzed C═N Bond Formation through a Rebound Hydrolysis Mechanism and Application in β-Lactam Synthesis. , 2019, Organic letters.

[18]  Y. Shao,et al.  Stereoselective Synthesis of Fully Substituted β-Lactams via Metal-Organo Relay Catalysis. , 2019, Organic letters.

[19]  F. Rominger,et al.  Gold(III)-Catalyzed Formal [3 + 2] Annulations of N-Acyl Sulfilimines with Ynamides for the Synthesis of 4-Aminooxazoles. , 2019, Organic letters.

[20]  Xiaoming Feng,et al.  Enantioselective Synthesis of 4-Hydroxy-dihydrocoumarins via Catalytic Ring Opening/Cycloaddition of Cyclobutenones. , 2019, Organic letters.

[21]  F. Rominger,et al.  Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles. , 2019, Angewandte Chemie.

[22]  F. Rominger,et al.  N-Pyridinyl Sulfilimines as a Source for α-Imino Gold Carbenes: Access to 2-Amino-Substituted N-Fused Imidazoles. , 2019, Organic letters.

[23]  W. Xiao,et al.  Visible-Light Photocatalytic Decarboxylative Alkyl Radical Addition Cascade for Synthesis of Benzazepine Derivatives. , 2018, Organic letters.

[24]  Jin‐Heng Li,et al.  Silver-Catalyzed Intermolecular [3 + 2]/[5 + 2] Annulation of N-Arylpropiolamides with Vinyl Acids: Facile Synthesis of Fused 2H-Benzo[b]azepin-2-ones , 2017 .

[25]  B. Ashfeld,et al.  Rearrangement of an Intermediate Cyclopropyl Ketene in a RhII-Catalyzed Formal [4 + 1]-Cycloaddition Employing Vinyl Ketenes as 1,4-Dipoles and Donor-Acceptor Metallocarbenes. , 2017, Organic letters.

[26]  R. B. Sunoj,et al.  Mechanism and Stereoselectivity in an Asymmetric N-Heterocyclic Carbene-Catalyzed Carbon-Carbon Bond Activation Reaction. , 2016, Organic letters.

[27]  J. Yoshida,et al.  The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling. , 2016, Journal of the American Chemical Society.

[28]  F. Glorius,et al.  Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations. , 2016, Journal of the American Chemical Society.

[29]  Xiangdong Hu,et al.  Four-Electron Electrocyclic Ring-Opening/Intermolecular [4+2] Cycloadditions of α-Hydroxycyclobutenones: Stereoselective Synthesis of Multiple Substituted δ-Lactams , 2016 .

[30]  Kazunobu Igawa,et al.  Direct thioamination of arynes via reaction with sulfilimines and migratory N-arylation. , 2015, Journal of the American Chemical Society.

[31]  P. Evans,et al.  Metal-free metathesis reaction of C-chiral allylic sulfilimines with aryl isocyanates: construction of chiral nonracemic allylic isocyanates. , 2014, Journal of the American Chemical Society.

[32]  J. Suico,et al.  Effects of the cholesteryl ester transfer protein inhibitor evacetrapib on lipoproteins, apolipoproteins and 24-h ambulatory blood pressure in healthy adults , 2014, The Journal of pharmacy and pharmacology.

[33]  K. Houk,et al.  Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles. , 2011, Angewandte Chemie.

[34]  L. Meijer,et al.  1-Azakenpaullone is a selective inhibitor of glycogen synthase kinase-3 beta. , 2004, Bioorganic & medicinal chemistry letters.

[35]  Y. Yamamura,et al.  Orally active, nonpeptide vasopressin V2 receptor antagonists: a novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and related compounds. , 1996, Journal of medicinal chemistry.

[36]  J. Proudfoot,et al.  Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones. , 1991, Journal of medicinal chemistry.

[37]  J. E. Babiarz,et al.  Synthesis and biological properties of (carboxyalkyl)amino-substituted bicyclic lactam inhibitors of angiotensin converting enzyme. , 1985, Journal of medicinal chemistry.

[38]  C. Moody,et al.  The chemistry of sulfilimines , 1977 .