Base-Mediated Cyclization of N-Benzyl Ketimines with Vinyl Sulfoxides: An Approach to Polysubstituted 1-Pyrrolines DOI

Tenglong Xu,

Donghao Wang, Zhen Liang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

A protocol for synthesizing polysubstituted 1-pyrrolines (3,4-dihydro-2H-pyrrole) via base-mediated [3 + 2] cycloaddition of vinyl sulfoxides with N-benzyl ketimines under mild conditions has been developed. The methodology exhibits exceptional functional group compatibility, demonstrating applicability to both terminal and internal sulfoxide substrates. Control experiments 1H NMR analyses have conducted propose a plausible reaction pathway. synthetic value this strategy further validated through successful gram-scale synthesis subsequent transformation the products into diverse derivatives.

Язык: Английский

Synthesis of Δ1-Pyrrolines via Formal (3 + 2)-Cycloaddition of 2H-Azirines with Enones Promoted by Visible Light under Continuous Flow DOI Creative Commons
Lorena S. R. Martelli, Lucas G. Furniel, Pedro H. O. Santiago

и другие.

ACS Omega, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

This work reports the first synthesis of Δ1-pyrrolines promoted by visible light under continuous flow, achieved through formal (3 + 2)-cycloaddition 2H-azirines to enones. A total 22 examples trisubstituted were prepared in only 30 min residence time, with 41-93% yield and diastereomeric ratios up 7:3. Furthermore, flow conditions also effective when chalcones used as starting materials, leading formation 7 tetrasubstituted pyrroles an overall ranging from 12 47%, via a photocatalyzed cycloaddition-oxidation sequence.

Язык: Английский

Процитировано

0
Nickel(II)-Catalyzed Unexpected [3 + 2] Cycloaddition/[3,3]-Rearrangement of N-Vinyl α,β-Unsaturated Nitrones with 2-Alkynyl Quinazolinones DOI

Xiaoting Qin,

Yue Leng,

Lin Ning

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 15, 2025

A nickel(II)-catalyzed unexpected [3 + 2] cycloaddition/[3,3]-rearrangement cascade reaction was developed for the preparation of various polysubstituted 1-pyrroline-tethered quinazolinones containing three contiguous stereocenters in moderate to good yields with high diastereoselectivity from N-vinyl cinnamaldehyde nitrones and 2-alkynyl quinazolinones. Polysubstituted pyrrolizine-tethered were obtained when replaced by chalcone nitrones. The present method features a broad substrate scope, [3,3]-rearrangement selectivity diastereoselectivity, two substituent bifurcated types N-heterocycles.

Язык: Английский

Процитировано

0
Base-Mediated Cyclization of N-Benzyl Ketimines with Vinyl Sulfoxides: An Approach to Polysubstituted 1-Pyrrolines DOI

Tenglong Xu,

Donghao Wang, Zhen Liang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

A protocol for synthesizing polysubstituted 1-pyrrolines (3,4-dihydro-2H-pyrrole) via base-mediated [3 + 2] cycloaddition of vinyl sulfoxides with N-benzyl ketimines under mild conditions has been developed. The methodology exhibits exceptional functional group compatibility, demonstrating applicability to both terminal and internal sulfoxide substrates. Control experiments 1H NMR analyses have conducted propose a plausible reaction pathway. synthetic value this strategy further validated through successful gram-scale synthesis subsequent transformation the products into diverse derivatives.

Язык: Английский

Процитировано

0