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

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
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
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