Sulfur‐Mediated Ring‐Opening Cyclization of Spirocyclopropanes for the Construction of Benzo[b]thiophene Skeleton DOI Creative Commons

Hisanori Nambu,

Yuki Seto,

Yuta Onuki

et al.

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: May 14, 2025

Abstract A novel approach for the construction of benzo[ b ]thiophene skeleton has been developed. Regioselective ring‐opening cyclization cyclohexane‐1,3‐dione‐2‐spirocyclopropanes using sodium hydrosulfide as a sulfur‐transfer reagent proceeded smoothly and subsequent addition an acid afforded corresponding tetrahydrobenzo[ ]thiophen‐4‐one derivatives in good to excellent yields. Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes could be also applied present protocol. In contrast, reaction monocyclic 1,1‐diacetyl‐2‐phenylcyclopropane with gave decomposition products instead desired product. This result suggests that spiro structure is crucial successful cyclization. One obtained from converted into 2‐substituted 4‐hydroxybenzo[ derivative while avoiding oxidation sulfide sulfoxide or sulfone. protocol provides alternative synthetic method access ]thiophenes without multisubstituted benzenes starting materials, which are often difficult prepare. To our knowledge, this first report synthesis cyclopropanes.

Language: Английский

Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes DOI Creative Commons
Hisanori Nambu,

Yuta Onuki,

Kana Aso

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4537 - 4540

Published: Jan. 1, 2024

A novel method was devised for regioselective ring expansion of spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2- trans -disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones without the formation any isomers.

Language: Английский

Citations

3
Synthesis of donor-acceptor type 1,1-bis(sulfonyl)cyclopropanes from active bis(sulfonyl)methylene compounds using sulfonium salts DOI

Kotaro Ezoe,

Koji Murakami, Keisuke Tomohara

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134514 - 134514

Published: Feb. 1, 2025

Language: Английский

Citations

0
Sulfur‐Mediated Ring‐Opening Cyclization of Spirocyclopropanes for the Construction of Benzo[b]thiophene Skeleton DOI Creative Commons

Hisanori Nambu,

Yuki Seto,

Yuta Onuki

et al.

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: May 14, 2025

Abstract A novel approach for the construction of benzo[ b ]thiophene skeleton has been developed. Regioselective ring‐opening cyclization cyclohexane‐1,3‐dione‐2‐spirocyclopropanes using sodium hydrosulfide as a sulfur‐transfer reagent proceeded smoothly and subsequent addition an acid afforded corresponding tetrahydrobenzo[ ]thiophen‐4‐one derivatives in good to excellent yields. Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes could be also applied present protocol. In contrast, reaction monocyclic 1,1‐diacetyl‐2‐phenylcyclopropane with gave decomposition products instead desired product. This result suggests that spiro structure is crucial successful cyclization. One obtained from converted into 2‐substituted 4‐hydroxybenzo[ derivative while avoiding oxidation sulfide sulfoxide or sulfone. protocol provides alternative synthetic method access ]thiophenes without multisubstituted benzenes starting materials, which are often difficult prepare. To our knowledge, this first report synthesis cyclopropanes.

Language: Английский

Citations

0