Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons DOI

Yuta Onuki,

Koga Yamazaki,

Yuto Masuda

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(15), P. 2536 - 2544

Published: Feb. 24, 2023

Abstract In this study, regio‐ and diastereoselective ring‐opening cyclization of spirocyclopropanes with phosphorus ylides stabilized by electron‐withdrawing groups were developed. The reaction various cyclohexane‐1,3‐dione‐2‐spirocyclopropanes bearing alkoxycarbonyl proceeded smoothly without any additives to provide the corresponding 6,7‐dihydroindan‐4‐ones in 32–87% yields. Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes also used reaction, producing products 1,2,3,6,7,8‐hexahydroazulen‐4‐ones 52–67% resulting [5.6]‐ [5.7]‐fused carbocyclic readily converted into highly substituted indanes azulenes, respectively, oxidation.

Language: Английский

Tandem Dearomative/Rearomative (3 + 2) Annulation of Aroyl-Substituted Donor–Acceptor Cyclopropanes with Benzothiazoles DOI

Subaramaniam Thangamalar,

Kannupal Srinivasan

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3903 - 3908

Published: March 6, 2023

A series of benzo[d]pyrrolo[2,1-b]thiazoles was synthesized by (3 + 2) annulation aroyl-substituted donor-acceptor cyclopropanes with benzothiazoles. The annulation, promoted a substoichiometric amount Sc(OTf)3, takes place through the formation respective dearomatized adducts, followed unexpected decarbethoxylative and dehydrogenative rearomatization to afford fully aromatized products. unusual reactivity is attributed presence an extra aroyl group in cyclopropanes.

Language: Английский

Citations

8
AlCl3-mediated ring-opening reactions of indoline-2-thiones with acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes DOI
Haojie Ma, Ke Gao, Xuelong Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6312 - 6316

Published: Jan. 1, 2023

A series of indolylthio-functionalized ketones were constructed via a ring-opening reaction, and the linear could be further transformed into dihydro-2 H -thiepino[2,3- b ]indoles.

Language: Английский

Citations

6
Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives DOI
Fatemeh Doraghi,

Mahmoud Ameli,

Somaye Karimian

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(13)

Published: March 27, 2024

Abstract Dibenzoazepine, dibenzoxazepine and dibenzothiazepine scaffolds are an important class of N ‐heterocycles that possess multiple biological activities. Due to the widespread application these motifs in drug discovery, synthesis tri‐cyclic seven‐membered imines/amines has gained huge attention chemists. In present review, we have highlighted recent advances functionalization cyclization reactions valuable organic compounds over last six years.

Language: Английский

Citations

2
B(C6F5)3/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes DOI
Zhen Liu,

Qing-Chun Qian,

Liming Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3247 - 3251

Published: April 1, 2024

Herein, we report an asymmetric aza-Diels–Alder reaction of quinoxalinones or benzoxazinones with unactivated dienes by utilizing a B(C6F5)3/chiral phosphoric acid catalyst to construct chiral six-membered N-heterocycles. Various electron-withdrawing and electron-donating groups were tolerated (up 99% yield ee) in the methodology only 2 mol % loading. Moreover, luminescence mechanism photophysical properties product tested used for anticounterfeiting QR codes.

Language: Английский

Citations

2
GaCl3‐Catalyzed [3 + 2]‐Cycloaddition/Esterification Cascade of Donor–Acceptor Cyclopropanes With Salicylaldehydes for the Synthesis of Tetrahydro‐4H‐Furo[3,2‐c]Chromen‐4‐Ones DOI
Zhiping Liu, Jie Pang,

Lijie Che

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 30, 2024

ABSTRACT A GaCl 3 ‐catalyzed [3 + 2]‐cycloaddition/intramolecular esterification cascade of donor–acceptor cyclopropane‐1,1‐diesters with salicylaldehydes has been reported. wide range tetrahydro‐4 H ‐furo[3,2‐ c ]chromen‐4‐ones have efficiently delivered in moderate to good yields. Mechanistic studies suggest that the reaction involves 2]‐cycloaddition followed by intramolecular access 4 ]chromenones.

Language: Английский

Citations

1
Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor–acceptor cyclopropanes: synthesis of γ-sulfoximino malonic diesters DOI
Satish G. More, Gurunath Suryavanshi

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2518 - 2529

Published: Jan. 1, 2022

Scandium triflate (Sc(OTf)3) catalyzed, mild, and regioselective ring-opening reaction of donor-acceptor (D-A) cyclopropanes has been developed using sulfoximines for the synthesis γ-sulfoximino malonic diesters. This protocol allows different N-alkyl in good to excellent yields (up 94%) with broad functional group tolerance. In this process, N-H C-C bonds are cleaved form new C-N C-H bonds. The feasibility method is supported by a gram-scale synthetic elaboration obtained product.

Language: Английский

Citations

6
Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons DOI

Yuta Onuki,

Koga Yamazaki,

Yuto Masuda

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(15), P. 2536 - 2544

Published: Feb. 24, 2023

Abstract In this study, regio‐ and diastereoselective ring‐opening cyclization of spirocyclopropanes with phosphorus ylides stabilized by electron‐withdrawing groups were developed. The reaction various cyclohexane‐1,3‐dione‐2‐spirocyclopropanes bearing alkoxycarbonyl proceeded smoothly without any additives to provide the corresponding 6,7‐dihydroindan‐4‐ones in 32–87% yields. Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes also used reaction, producing products 1,2,3,6,7,8‐hexahydroazulen‐4‐ones 52–67% resulting [5.6]‐ [5.7]‐fused carbocyclic readily converted into highly substituted indanes azulenes, respectively, oxidation.

Language: Английский

Citations

3