Construction of 1,4‐Oxazepinones via a Cascade Aza‐Michael/SN2 Annulation of Trifluoromethyl Pyrazole‐derived Oxadienes with a‐Bromohydroxamates DOI
Kai‐Chuan Yang, Zhengwen Li, Yuchi Wang

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 21, 2024

Abstract A highly efficient cascade aza‐MIRC (Michael Induced Ring Closure) reaction between trifluoromethylpyrazole (TFPZ)‐derived oxadienes and a ‐bromohydroxamates has been developed for the construction of 1,4‐oxazepinone derivatives. The proceeds smoothly under mild conditions via Aza‐Michael addition/intramolecular S N 2 sequence, features broad substrate scope, transition‐metal free, operational simplicity etc. utility versatile protocol was also demonstrated by gram‐scale valuable synthetic transformations.

Язык: Английский

Acid-Modulated Construction of Cyclopenta[b]indole and Cyclohepta[b]indole via Unprecedented C3/C2 Carbocation Rearrangement DOI

Shao‐Cong Zhan,

Jing Sun,

Qiu Sun

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5440 - 5456

Опубликована: Апрель 3, 2023

p-TsOH-catalyzed cycloaddition of various 3-vinylindoles and (indol-2-yl)diphenylmethanols in acetonitrile gave the functionalized cyclopenta[b]indoles good yields with high diastereoselectivity via [3 + 2] reaction. More importantly, FeCl3-catalyzed annulation reaction afforded unexpected cyclohepta[1,2-b:4,5-b']diindoles satisfactory yields, which a formal [4 3] an unprecedented C3/C2 carbocation rearrangement were first confirmed by determination single-crystal structure.

Язык: Английский

Процитировано

16

Synthesis of Polycyclic Imidazolidinones via Cascade [3 + 2]-Annulation of β-Oxo-acrylamides with Cyclic N-Sulfonyl Imines DOI
Lei Xie,

Chenyi Zhao,

Zhaoxue Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(22), С. 15805 - 15816

Опубликована: Окт. 31, 2023

An Et3N-catalyzed cascade [3 + 2]-annulation of β-oxo-acrylamides with cyclic N-sulfonyl ketimines or sulfamate-derived imines is developed under mild reaction conditions, which provides a concise and efficient route to access valuable sultam- sulfamidate-fused imidazolidinone derivatives in good excellent yields (80–95% yields) diastereoselectivities (>20:1 drs). The current protocol features atom economy, transition-metal-free process, broad functional group tolerance. Moreover, the asymmetric variant 2]-cycloaddition was achieved presence diphenylethanediamine quinine-based bifunctional squaramide organocatalysts C-1 C-11, giving corresponding chiral polycyclic imidazolidinones 68–90% 25–94% ees >20:1 drs all cases.

Язык: Английский

Процитировано

10

A [4+3] annulation of benzofuran-derived azadienes and α-bromohydroxamates for the synthesis of benzofuran-fused 1,4-diazepinones DOI

Qing-Yun Fang,

Li‐Ming Zhao

Chemical Communications, Год журнала: 2020, Номер 56(90), С. 14079 - 14082

Опубликована: Янв. 1, 2020

A Cs2CO3-mediated formal [4+3] cycloaddition involving benzofuran-derived azadienes (BDAs) and α-bromohydroxamates to afford benzofuran-fused 1,4-diazepinones is established. This the first example of using BDAs for construction seven-membered dinitrogen-fused heterocycles. strategy not only enriches chemistry but also provides an interesting class bioisosteres 1,4-benzodiazepine.

Язык: Английский

Процитировано

25

Palladium-Catalyzed Asymmetric Cascade Intramolecular Cyclization/Intermolecular Michael Addition Reaction of Allenyl Benzoxazinones with 1-Azadienes DOI

Huawei Lin,

Xianru Yang,

Wenyue Ning

и другие.

Organic Letters, Год журнала: 2022, Номер 24(51), С. 9442 - 9446

Опубликована: Дек. 20, 2022

We herein designed and synthesized allenyl benzoxazinones of a novel type, which were then involved in Pd-catalyzed asymmetric cascade intramolecular cyclization/intermolecular Michael addition reaction with 1-azadienes. A broad range chiral C2-functionalized quinoline derivatives afforded moderate to good yields (up 93%) high enantioselectivities 93% ee) this reaction.

Язык: Английский

Процитировано

16

Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons DOI
Kai‐Kai Wang,

Yanli Li,

Rongxiang Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(12), С. 8158 - 8169

Опубликована: Июнь 8, 2022

The additive-free [3 + 2] annulation from isatins, amino acids with 2-styrylbenzoxazoles, was described, providing a series of functional and structurally complex 3,3'-pyrrolidinyl-spirooxindole derivatives containing four contiguous two quaternary stereogenic centers in high yields (up to 95%) excellent diastereoselectivities >25:1 dr). Interestingly, the reaction exhibits switchable regioselectivity depending on substrate acids. With proline or thioproline as substrate, afforded α-regioselective spirooxindole skeletons. In contrast, when piperidine acid is provided γ-regioselective

Язык: Английский

Процитировано

15

Synthesis of polysubstituted spiroazepines via [4 + 3] annulation reaction of ninhydrin-derived Morita−Baylis−Hillman carbonates with 1‑heterodienes DOI
Kai‐Kai Wang, Yafei Li, R. Bi

и другие.

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 141478 - 141478

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Organocatalytic cascade nucleophilic/aza-Michael addition reactions: metal-free catalytic strategy for the synthesis of hydantoins DOI
Lei Xie, Lei Sun,

Ping Wu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 21(11), С. 2295 - 2300

Опубликована: Ноя. 17, 2022

Lewis base-catalyzed cascade nucleophilic/aza-Michael addition reaction of N-alkoxy β-oxo-acrylamides with isocyanates has been developed to afford various highly functionalized hydantoin derivatives in 80-98% yields under mild conditions. The intriguing features this method include metal-free conditions, low catalyst loading, broad substrate scope and short time.

Язык: Английский

Процитировано

11

Brønsted Base‐Catalyzed Tandem [2+4] Annulation/Tautomerization/Aromatization Reaction of α‐Alkylidene Succinimides with 5‐Alkenyl Thiazolones DOI
Chunhao Yuan, Huimin Yang, Qi Gong

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(13), С. 3336 - 3347

Опубликована: Май 6, 2021

Abstract A Brønsted base‐catalyzed tandem [2+4] annulation/tautomerization/aromatization reaction of α‐alkylidene succinimides with 5‐alkenyl thiazolones has been developed for synthesis functionalized thiazolo pyrones under mild conditions. The prepared show fluorescent properties. magnified image

Язык: Английский

Процитировано

14

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds DOI Open Access
Julian Garrec, Alexis Archambeau,

Anaïs Scuiller

и другие.

Synlett, Год журнала: 2021, Номер 32(10), С. 981 - 986

Опубликована: Май 19, 2021

Abstract A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear have also been involved yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

Язык: Английский

Процитировано

13

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions DOI

Deeksha,

Ritesh Singh

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(47)

Опубликована: Окт. 10, 2022

Abstract Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively a 3‐unit synthon 1,3 dipoles create N‐heterocycles via cycloaddition reactions, wherein cation served electrophilic counterpart. Recently, new variations been reported, including usage 1,4 dipole domino and unique alkylating ability heteroatoms. This review article provides an update recent developments this area prevailing mechanistic insight.

Язык: Английский

Процитировано

9