Diastereoselective Construction of Spirocyclic Isobenzofurans via a Tandem Michael Addition/5-Exo-dig Cyclization Reaction DOI

Shaghayegh Mehdidoust,

Saideh Rajai‐Daryasarei,

S. Sina Hosseini

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16613 - 16621

Published: Oct. 31, 2024

A practical approach for rapid and efficient access to spirocyclic isobenzofurans is described. The reaction proceeds through the cycloaddition of 1,6-ynenone derivatives 4-nitro-1,3-diarylbutan-1-ones, promoted by Cs

Language: Английский

Synthesis of gem‐Difluorocyclobutane‐Fused Indolines via Ruthenium‐Catalyzed Defluorinative Annulation of Trifluoromethyl Carbenoids with 2‐Alkenylanilines DOI
Hao Tan, Haosheng Li,

Shaofeng Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1059 - 1063

Published: Jan. 12, 2024

Abstract A ruthenium‐catalyzed defluorinative annulation of 2‐alkenylanilines with α‐trifluoromethyl diazoester or diazoketones is described. The reaction has broad substrate scope, affording a range gem ‐difluorocyclobutane‐fused indolines in moderate to good yields cis ‐configuration. Mechanistic investigations indicate that the proceeds through sequential N−H insertion/C−F bond cleavage/[2+2] cycloadditon process. α‐Trifluoromethyl‐α‐diazo reagents serve as ‐difluorinated C2 subunits by cleaving one C−F bond.

Language: Английский

Citations

1
A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK DOI

Jingxiong Lai,

You Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(15), P. 2066 - 2069

Published: Jan. 1, 2024

A CH 3 OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.

Language: Английский

Citations

1
Divergent Synthesis of Naphthalenone Spiroindanediones or 4‐Acyl‐1‐naphthols from Aryl Enaminones Featuring Reuse of Dimethylamine DOI

Chun Xia Yang,

Bin Li, Xinying Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(15), P. 3372 - 3378

Published: May 29, 2024

Abstract Presented herein is a switchable synthesis of naphthalenone spiroindanediones or 4‐acyl‐1‐naphthols via condition‐controlled divergent cascade reactions aryl enaminones with diazoindanediones. When the reaction was carried out in presence an oxidative additive, spiroindanedione formed through C( sp 2 )−H alkylation followed by simultaneous spiroannulation and elimination dimethylamine. acid on other hand, 4‐acyl‐1‐naphthol ring opening moiety attacked situ released In addition, are suitable for gram‐scale applications compatible variety substrates. Moreover, naphthol products allow structural elaborations hybridization drug, thus further enhancing value this developed method.

Language: Английский

Citations

1
Reactivity of Acceptor-Acceptor Diazo-Pyrazolones with Allyl Thioethers under Visible Light: Access to Homoallyl and Bis-Homoallyl Sulfides, Spiropyrazolones-Pesticide Analogues and Photo-Flow Synthesis DOI Creative Commons

Onkar S. Bankar,

Chhabi Pal,

Debasish Laha

et al.

Published: Aug. 13, 2024

Pyrazolone framework has been greatly explored for various applications owing to their presence in many bioactive compounds. The novel reactivity of less selective and more reactive acceptor-acceptor kind diazo pyrazolone (DIPOL) under visible light the first time. We have successfully demonstrated reaction DIPOL different allyl thioethers blue construct a wide variety products including pesticidal analogue exclusively excellent chemo-selectivities good yields. Moreover, possible side emanating from ketene were not observed. This protocol works smoothly environmentally benign solvent inert free condition. practicality extended photo-flow also direct exposure sunlight.

Language: Английский

Citations

1
The Reactivity of Acceptor-Acceptor Diazo Pyrazolones with Allyl Thioethers under Visible Light: Access to Homoallyl Sulfides, Spiropyrazolones - Pesticide Analogues and Photoflow Synthesis DOI

Onkar S. Bankar,

Chhabi Pal,

Debasish Laha

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9191 - 9197

Published: Oct. 23, 2024

The novel reactivity of a less selective and more reactive acceptor-acceptor kind diazo pyrazolone (DIPOL) has been explored under visible light for the first time. We have successfully demonstrated reaction DIPOL different allyl thioethers blue to construct wide variety products including pesticidal analogue exclusively in excellent chemoselectivity good yields. Moreover, possible side emanating from ketene were not observed. This protocol works smoothly an environmentally benign solvent inert free conditions. practicality extended photoflow reaction, also, direct exposure sunlight.

Language: Английский

Citations

1
Recent advances in developing highly atom-economic C–H annulation reactions in water DOI
Tanmay Chatterjee, Paramita Pattanayak,

Appanapalli N. V. Satyanarayana

et al.

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2023, Volume and Issue: 41, P. 100826 - 100826

Published: April 24, 2023

Language: Английский

Citations

3
Free Amine-Directed Redox Neutral Ruthenium(II) Catalysis toward Regioselective Synthesis of Heterobiaryls DOI
Suman Ghosh,

Mainak Koner,

Anusree A. Kunhiraman

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2987 - 2992

Published: April 2, 2024

A regioselective coupling of ortho-heteroaryl anilines and 7-oxabenzonorbornadienes has been developed by leveraging free amine-directed redox-neutral Ru(II) catalysis. This protocol facilitates formal C-2 arylation the indole moiety under mild conditions to offer valuable heterobiaryls in high yields. The reaction displays a broad substrate generality scalability retains efficacy presence diverse pharmacophore scaffolds. Moreover, products bearing amine group were successfully employed Mg(NTf2)2-catalyzed double Michael addition cascade, which led synthesis intricate indole- pyrrole-fused azaheterocycles.

Language: Английский

Citations

0
2‐Vinylaniline in the synthesis of heterocycles: Recent advances DOI
Fatemeh Doraghi,

Hamed Navid,

Somaye Karimian

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(7), P. 1180 - 1199

Published: May 21, 2024

Abstract 2‐Vinylanilines are readily accessible substrates, which undoubtedly one of the best candidates for construction diversely nitrogen‐containing heterocyclic compounds. Owing to amine and alkenyl groups in their structures, these frameworks offer a facile, direct, selective synthetic method. This review describes various cyclization reactions involving 2‐vinylanilines catalyzed by transition metals, or under metal‐free conditions.

Language: Английский

Citations

0
Efficient Access to Spiro[Quinazoline-Thiophen](Thi)Ones Via Acetic Acid Catalyzed [3 + 2] Annulation of Quinazolin(Thi)One Enamines with Dithianediol DOI

Jingxi Fang,

Zhentao Pan,

Yingbo Rao

et al.

Published: Jan. 1, 2024

Download This Paper Open PDF in Browser Add to My Library Share: Permalink Using these links will ensure access this page indefinitely Copy URL DOI

Language: Английский

Citations

0
Efficient access to spiro[quinazoline-thiophen](thi)ones via acetic acid mediated [3 + 2] annulation of quinazolin(thi)one enamines with dithianediol DOI

Jingxi Fang,

Zhentao Pan,

Yingbo Rao

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 138, P. 154965 - 154965

Published: Feb. 26, 2024

Language: Английский

Citations

0