Cargando…

Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor–acceptor (DA)-aminocyclopropanes via an ytte...

Descripción completa

Detalles Bibliográficos
Autores principales:	Preindl, Johannes, Chakrabarty, Shyamal, Waser, Jérôme
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Royal Society of Chemistry 2017
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637460/ https://www.ncbi.nlm.nih.gov/pubmed/29147541 http://dx.doi.org/10.1039/c7sc03197a

Ejemplares similares

Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
por: Pirenne, Vincent, et al.
Publicado: (2021)

Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes
por: Muriel, Bastian, et al.
Publicado: (2019)

Enantioselective N-heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums
por: Flanigan, Darrin M., et al.
Publicado: (2017)

A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation
por: Wu, Zijun, et al.
Publicado: (2018)

C–H activation-annulation on the N-heterocyclic carbene platform
por: Dutta, Champak, et al.
Publicado: (2018)

N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations
por: Sharique, Mohammed, et al.
Publicado: (2020)

Editorial: Six-membered heterocycles: their synthesis and bio applications
por: Shiri, Pezhman, et al.
Publicado: (2023)

Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
por: Seoane, Andrés, et al.
Publicado: (2014)

N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
por: Chen, Xiang-Yu, et al.
Publicado: (2017)

A switchable redox annulation of 2-nitroarylethanols affording N-heterocycles: photoexcited nitro as a multifunctional handle
por: Wang, Bin, et al.
Publicado: (2022)

π-Extension of heterocycles via a Pd-catalyzed heterocyclic aryne annulation: π-extended donors for TADF emitters
por: Spence, Katie A., et al.
Publicado: (2022)

Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides
por: Pichler, Mathias, et al.
Publicado: (2015)

N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
por: Sato, Hiroki, et al.
Publicado: (2022)

Organocatalytic asymmetric chlorinative dearomatization of naphthols
por: Yin, Qin, et al.
Publicado: (2015)

Regio- and diastereoselective dearomatizations of N-alkyl activated azaarenes: the maximization of the reactive sites
por: Miao, Hong-Jie, et al.
Publicado: (2019)

Three-membered cyclic digermylenes stabilised by an N-heterocyclic carbene
por: Dong, Zhaowen, et al.
Publicado: (2021)

Nanocatalysts: applications for the synthesis of N-containing five-membered heterocycles
por: Jangir, Nidhi, et al.
Publicado: (2022)

Ring expansion of alumoles with organic azides: selective formation of six-membered aluminum–nitrogen heterocycles
por: Drescher, Regina, et al.
Publicado: (2020)

Functionalized spirolactones by photoinduced dearomatization of biaryl compounds
por: Li, Hongji, et al.
Publicado: (2019)

Correction: Dearomatization of benzopyrylium triflates with sulfoxonium ylides
por: Leveille, Alexandria N., et al.
Publicado: (2023)

Design of C(1)-symmetric tridentate ligands for enantioselective dearomative [3 + 2] annulation of indoles with aminocyclopropanes
por: Wang, Hai-Xia, et al.
Publicado: (2023)

Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
por: Zhao, Changgui, et al.
Publicado: (2018)

N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation
por: Peng, Qiupeng, et al.
Publicado: (2020)

Enantioselective dearomatization reactions of heteroarenes by anion-binding organocatalysis
por: Aleksiev, Martin, et al.
Publicado: (2023)

Mechanistic insights into the insertion and addition reactions of group 13 analogues of the six-membered N-heterocyclic carbenes: interplay of electrophilicity, basicity, and aromaticity governing the reactivity
por: Zhang, Zheng-Feng, et al.
Publicado: (2021)

Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols
por: Wu, Wen-Ting, et al.
Publicado: (2016)

A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles
por: García-Vázquez, Víctor, et al.
Publicado: (2021)

Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands
por: Kondo, Hiroki, et al.
Publicado: (2017)

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
por: Zhang, Yu, et al.
Publicado: (2017)

Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation
por: Huang, Xin, et al.
Publicado: (2020)

Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
por: Song, Xiaoxiao, et al.
Publicado: (2014)

N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
por: Ni, Qijian, et al.
Publicado: (2015)

Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis
por: Zhao, He, et al.
Publicado: (2022)

Microwave assisted synthesis of five membered nitrogen heterocycles
por: Meera, Gopinadh, et al.
Publicado: (2020)

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
por: Nicolai, Stefano, et al.
Publicado: (2022)

α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
por: Viji, Mayavan, et al.
Publicado: (2020)

Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges
por: Volkova, Yulia, et al.
Publicado: (2023)

Electrooxidative dearomatization of biaryls: synthesis of tri- and difluoromethylated spiro[5.5]trienones
por: Zhang, Yan, et al.
Publicado: (2021)

Impact of Heterocycle Annulation on NIR Absorbance in Quinoid Thioacene Derivatives
por: Hou, Peng, et al.
Publicado: (2022)

Electrocatalytic redox neutral [3 + 2] annulation of N-cyclopropylanilines and alkenes
por: Wang, Qi, et al.
Publicado: (2020)

Cannot write session to /tmp/vufind_sessions/sess_sgdhtslvtrf1skf4j4fm9o28pm