Selective Synthesis of Dihydro- and Dehydrogenated Spirocyclopenta[b]indoles via Acid-modulated [3+2] Cycloaddition Reaction DOI
Dongmei Liu,

Shao‐Cong Zhan,

Ren-Jie Fang

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 140792 - 140792

Published: Nov. 1, 2024

Language: Английский

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction DOI Creative Commons
Xiuyu Chen, Ying Han,

Jing Sun

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1436 - 1443

Published: June 28, 2024

An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates was developed by a three-component reaction. In absence any catalyst, reaction alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded high yields with diastereoselectivity. The finished situ generation activated 5-(alkylimino)cyclopenta-1,3-dienes from addition isocyanide to two molecules sequential formal [3 + 2] cycloaddition 1,4-dihydropyridine.

Language: Английский

Citations

4
Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction DOI

Yu‐Wei He,

Li Huang, Kun Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10854 - 10866

Published: July 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Language: Английский

Citations

4
Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives DOI
Daqian Wang, Xing Liu,

Jing Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15472 - 15489

Published: Oct. 15, 2024

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols ortho-vinylphenols with MBH carbonates isatins under mild metal-free conditions. The selective generation different kinds derivatives was successfully achieved employing substituted isatin-derived ortho-N-tosyliminophenols ortho-vinylphenols. features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, atomic economy.

Language: Английский

Citations

4
Convenient synthesis of chromene-fused spirocyclopentane-1,2-dioxindoles via base promoted annulation reaction DOI
Kun Huang, Ting Tang, Ying Han

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155455 - 155455

Published: Jan. 8, 2025

Language: Английский

Citations

0
Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins DOI
Kun Huang, Kaihua Zhang,

Ziying Xiao

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155452 - 155452

Published: Jan. 13, 2025

Language: Английский

Citations

0
Spiro-Heterocycles: Recent Advances in Biological Applications and Synthetic Strategies DOI

D Basavaraja,

Sameer Kumar Devarakonda, A. S.

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134468 - 134468

Published: Jan. 1, 2025

Language: Английский

Citations

0
Construction of Spiro[indoline‐3,2′‐pyrrolo[2,1‐a]Isoquinoline] and Spiro[indoline‐3,2′‐pyrrolo[1,2‐a]Quinoline] via Isocyanide‐Based Three‐Component Reaction DOI
Dongmei Liu,

Yu‐Wei He,

Ying Han

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(4)

Published: Jan. 1, 2025

Abstract A convenient synthetic protocol for novel spiro[indoline‐3,2′‐pyrrolo[2,1‐ a ]isoquinoline] and spiro[indoline‐3,2′‐pyrrolo[1,2‐ ]quinoline] motifs was successfully developed by three‐component reaction of isoquinoline (quinoline), cyclohexyl isocyanide, isatylidene malononitriles. In the absence any catalyst, isoquinoline, malononitriles in refluxing dichloromethane gave functionalized ]isoquinolines] good yields with high diastereoselectivity. However, similar quinoline afforded ]quinolines] about 2:1

Language: Английский

Citations

0
Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles DOI Creative Commons

Ziying Xiao,

Jing Sun,

Chao‐Guo Yan

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 286 - 295

Published: Feb. 6, 2025

In this paper, the nucleophilic substitution reactions of various N- and P-containing nucleophiles to MBH carbonates isatins were investigated. Diverse functionalized 3-substituted oxindole derivatives successfully prepared in satisfactory yields with high diastereoselectivity. addition, base-promoted dimerization isatin afforded ethylene-bridged bis(3-methylene)oxindole nearly 4:1 diastereomeric ratios. The relative configurations polycyclic compounds clearly elucidated by determination several single crystal structures.

Language: Английский

Citations

0
Synthetic Protocol for Pyrido[2,3-c]pyridazine and Pyrido[3,2-e][1,2]oxazine Scaffolds via a [4 + 2] Cycloaddition Reaction DOI
Xiuyu Chen,

Jing Sun,

Ying Han

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Here, we revealed a convenient synthetic protocol for unique pyrido[2,3-c]pyridazine and pyrido[3,2-e][1,2]oxazine scaffolds with excellent regioselectvity diastereoselectivity. The functionalized pyrido[2,3-c] pyridazines were successfully synthesized via Cs2CO3-promoted [4 + 2] cycloaddition reaction of α-halogenated N-tosylhydrazones or N-acylhydrazones 5,6-unsubstituted 1,4-dihydropyridines under mild conditions. Additionally, the similar base-promoted α-chlorogenated oximes afforded pyrido[3,2-e][1,2]oxazines in satisfactory yields. features this included conditions, broad substrate scopes, high functional group tolerance, significant atomic economy.

Language: Английский

Citations

0
Convenient Synthesis of Dihydrobenzofuran‐Fused Spirocyclopentane‐1,2‐Diindolinone Scaffolds DOI
Ting Tang, Ying Han, Chao‐Guo Yan

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract The diverse functionalized dihydrobenzofuran‐fused spirocyclopentane‐1,2‐diindolin‐one scaffolds were conveniently synthesized by base promoted domino cyclization reaction of MBH (Morita‐Baylis‐Hillmann) carbonates isatins and 3‐( o ‐hydroxybenzylidene)indolin‐2‐ones. reactions maleimides formates with ‐hydroxybenzylidene)indolin‐2‐ones afforded polycyclic dispiro[indoline‐3,4′‐benzofuro[2′,3′:1,5]cyclopenta[1,2‐ c ]pyrrole‐5′,3′′‐indolines] dispiro[indoline‐3,1′‐cyclopenta[ b ]benzofuran‐2′,3′′‐indolines] in good yields high diastereoselectivity. More importantly, DMAP facilitated annulation nitriles selectively resulted dispiro[indoline‐3,1′‐cyclopentane‐2′,3′′‐indolines], while Cs 2 CO 3 gave relative configurations the various compounds clearly elucidated determination several single crystal structures.

Language: Английский

Citations

1