[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture DOI
Yang Li,

Wei‐Fang Zuo,

Jianhua Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(2), P. 269 - 276

Published: Nov. 30, 2023

Abstract Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one the rare examples that harness enaminone C−N bond cleavage to engineer relevant skeletons biological interest. Moreover, propose plausible mechanistic explanation elucidate outstanding chemical outcomes observed, thereby enriching synthetic toolbox chemistry α‐haloamide‐mediated reactions.

Language: Английский

Heteroannulation of Arynes with α-Bromodifluorohydroxamates: An Efficient and General Approach to Access 2,2-Difluoro Indoxyls DOI

Deeksha,

Ritesh Singh

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5682 - 5688

Published: June 27, 2024

Herein, we report the first general approach to access

Language: Английский

Citations

4
Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate DOI

Anaïs Scuiller,

Nicolas Casaretto, Alexis Archambeau

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9941 - 9945

Published: July 10, 2023

Cycloaddition of azaoxyallyl cations or other C─(C═O)─N synthon precursors is a well-established route toward lactams and N-heterocycles, but despite the wide synthetic scope this approach, enantioselective versions remain scarce. We herein report 5-vinyloxazolidine-2,4-diones (VOxD) as suitable precursor new palladium-π-allylpalladium intermediate. In presence electrophilic alkenes, (3 + 2) γ-lactam cycloadducts could be formed with high level diastereo- enantioselectivity.

Language: Английский

Citations

8
Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update DOI Creative Commons
Franca M. Cordero, Donatella Giomi, Fabrizio Machetti

et al.

Reactions, Journal Year: 2024, Volume and Issue: 5(3), P. 492 - 566

Published: Aug. 16, 2024

The present review is a comprehensive update of the synthesis monocyclic β-lactams via cycloaddition reactions. According to IUPAC definition cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. years 2019–2022 are covered by cited literature. focus on synthetic aspects with emphasis structural scope, reaction conditions, mechanistic aspects, selectivity results. Selected significant data related biological activities applications also highlighted.

Language: Английский

Citations

3
Divergent Reaction of Indoline‐derived Azadienes withα‐Bromohydroxamates: Synthesis of Spiro‐indolinepyrrolidinones and Indoline‐fused Diazepinones DOI
Hai‐Shan Jin,

Qing‐Yun Fang,

Jin‐Qi Wang

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(31)

Published: March 21, 2023

A divergent reaction of indoline-derived azadienes with α-bromohydroxamates for the selective synthesis spiro-indolinepyrrolidinones and indoline-fused diazepinones was disclosed. This sequence involved an initial formation five-membered spirocyclic products followed by intramolecular ring-opening ring expansion to produce seven-membered diazepinones. We demonstrated that controlling time could modulate pathway different molecular frameworks same set substrates. Based on experimental results, mechanism also discussed proposed explain phenomena observed in process.

Language: Английский

Citations

6
Metal-free and enantioselective synthesis of 1,4-benzoxazepines frompara-quinone methide derivatives and α-bromohydroxamates DOI

Suo‐Suo Qi,

Xin Luo, Xiaoping Sun

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(57), P. 8822 - 8825

Published: Jan. 1, 2023

A sequential asymmetric conjugate addition/cyclisation of α-bromohydroxamates with para-quinone methide derivatives has been developed, which provides enantioenriched 1,4-benzoxazepines in generally high yields (up to 95%) and good enantioselectivities 97 : 3 er). This protocol not only offers a novel straightforward strategy for constructing chiral 1,4-benzoxazepines, but also demonstrates the potential as three-atom synthons cyclisation reactions.

Language: Английский

Citations

5
Diastereo- and Enantioselective (3+2) Cycloaddition of a New Palladium-Aza-Oxyallyl Intermediate DOI Creative Commons

Anaïs Scuiller,

Nicolas Casaretto, Alexis Archambeau

et al.

Published: Feb. 23, 2023

Cycloaddition of azaoxyallyl cations or other C-(C=O)-N synthon precursors is a well-established route towards lactams and N-heterocycles but, despite the wide synthetic scope this approach, enantioselective versions remain scarce. We herein report 5-vinyloxazolidine-2,4-diones (VOxD) as suitable precursor chiral palladium-aza-oxyallyl intermediates. In presence electrophilic alkenes, (3+2) -lactam cycloadducts could be formed with high level diastero- enantioselectivity.

Language: Английский

Citations

4
A concise approach to 2-pyrrolin-5-one scaffold construction from α-halohydroxamates and β-keto compounds DOI
Wenjie Lan, Xuan Yu, Mengzhu Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(37), P. 7535 - 7540

Published: Jan. 1, 2023

A concise approach to the construction of 2-pyrrolin-5-one scaffold was developed via a one-pot reaction with formal [3 + 2] annulation/elimination between β-keto nitrile/β-keto ester and unsubstituted α-halohydroxamates.

Language: Английский

Citations

4
Base-mediated [4 + 3] annulation of α-halogen hydroximate with o-QMs: Facile access to 1, 4-benzoxazepine scaffold DOI
Wenjie Lan, Xiao‐Xu Gao, Mengzhu Li

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 136, P. 154911 - 154911

Published: Jan. 13, 2024

Language: Английский

Citations

1
[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture DOI
Yang Li,

Wei‐Fang Zuo,

Jianhua Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(2), P. 269 - 276

Published: Nov. 30, 2023

Abstract Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one the rare examples that harness enaminone C−N bond cleavage to engineer relevant skeletons biological interest. Moreover, propose plausible mechanistic explanation elucidate outstanding chemical outcomes observed, thereby enriching synthetic toolbox chemistry α‐haloamide‐mediated reactions.

Language: Английский

Citations

1