DABCO-mediated synthesis of aromatic esters from phenols, naphthols or 3-hydroxypyridines and aryl acyl peroxides at room temperature DOI Creative Commons

Liyuan Yan,

Haibo Zhu, Qian Li

и другие.

ARKIVOC, Год журнала: 2022, Номер 2022(9), С. 40 - 50

Опубликована: Авг. 25, 2022

An efficient and practical method for the synthesis of aromatic esters from aryl acyl peroxides phenols, naphthols or 3-hydroxypyridines at room temperature was realized.A series were synthesized in high yields with excellent selectivity presence 1,4-diaza[2.2.2]bicyclooctane (DABCO) without use transition-metals acid catalysts.This operation is simple, it has a good compatibility various functional groups, especially heterocyclic pyridine substrates.

Язык: Английский

Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds DOI

Jing Sun,

Xueyan Liu, Qiu Sun

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11562 - 11580

Опубликована: Июль 27, 2023

Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.

Язык: Английский

Процитировано

23

An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds DOI
Daqian Wang,

Jing Sun,

Ying Han

и другие.

Organic Letters, Год журнала: 2022, Номер 24(42), С. 7790 - 7795

Опубликована: Окт. 14, 2022

We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation Morita-Baylis-Hillman (MBH) carbonates isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex compounds were conveniently synthesized in satisfactory yields and high diastereoselectivity. This provides a swift convenient approach assembly diverse highly functionalized spirooxindoles also features broad substrate scope, molecular convergence, excellent atomic economy.

Язык: Английский

Процитировано

26

Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins DOI
Dan Liu,

Jing Sun,

Qiu Sun

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(2), С. 540 - 547

Опубликована: Дек. 10, 2022

An efficient synthetic protocol for the selective construction of spiro[indoline-3,5′-pyrrolo[3,4- b ]azepines] and spiro[indoline-3,3′-pyrroles] via a cycloaddition reaction α,β-unsaturated aldimines MBH adducts isatins was successfully developed.

Язык: Английский

Процитировано

24

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

Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides DOI

Liu‐Na Pan,

Jing Sun,

Xueyan Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(35), С. 7099 - 7104

Опубликована: Янв. 1, 2022

An efficient method to construct unique spiro[indoline-3,4′-pyrrolo[3,4- b ]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates isatins with β-enamino maleimides under mild conditions.

Язык: Английский

Процитировано

20

Regioselective and Diastereoselective Construction of Diverse Dispiro-Indanone-Fluorenone-Oxindole Motifs DOI
Dan Liu,

Jing Sun,

Ying Han

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17181 - 17196

Опубликована: Ноя. 28, 2023

A convenient synthetic protocol for regioselective and diastereoselective construction of complex dispiro-indanone-fluorenone-oxindole motifs was developed by the base-promoted annulation reaction bindone MBH carbonates isatins adjusting conditions. DABCO promoted in DCM at room temperature, affording dispiro[indene-2,4′-fluorene-1′,3″-indoline] derivatives good yields with high diastereoselectivity. Triethylamine two molecular 1,3-indanediones esters ethanol elevated temperature selectively gave dispiro[indene-2,4′-fluorene-3′,3″-indolines] moderate yields. However, triethylamine excess refluxing ethanol, Z-isomer as major product E-isomer minor product.

Язык: Английский

Процитировано

12

Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles DOI
Xing Liu, Daqian Wang,

Jing Sun

и другие.

Journal of Molecular Structure, Год журнала: 2024, Номер 1304, С. 137684 - 137684

Опубликована: Фев. 4, 2024

Язык: Английский

Процитировано

5

Recent applications of 1,3-indanedione in organic transformations for the construction of fused- and spiro scaffolds DOI
Suven Das

Tetrahedron, Год журнала: 2022, Номер 122, С. 132954 - 132954

Опубликована: Авг. 9, 2022

Язык: Английский

Процитировано

19

Domino reaction of bindone and 1,3-dipolarophiles for the synthesis of diverse spiro and fused indeno[1,2-a]fluorene-7,12-diones DOI
Dan Liu, Xueyan Liu,

Jing Sun

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(24), С. 4964 - 4969

Опубликована: Янв. 1, 2022

Base promoted domino reaction of bindone ([1,2′-biindenylidene]-1′,3,3′-trione) with common 1,3-dipolarophiles showed interesting molecular diversities.

Язык: Английский

Процитировано

17

Tandem ring-opening and formal [3 + 2] cycloaddition of furo[2,3-d]pyrimidine-2,4-diones DOI
Li Huang, Ying Han,

Jing Sun

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 6028 - 6033

Опубликована: Янв. 1, 2023

The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles such as 2-arylidene-1,3-indanediones, 2-(o-hydroxybenzylidene)-1,3-indanediones and 3-methyleneoxindoles with functionalized furo[2,3-d]pyrimidine-2,4-diones was systematically investigated. This provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds including dispiro[indene-2,3'-cyclopentane-1',5''-pyrimidines], dispiro[indoline-3,3'-cyclopentane-1',5''-pyrimidines] spiro[cyclopenta[c]indeno[1,2-b]chromene-3,5'-pyrimidines] in good yields high diastereoselectivity. believed to proceed via sequential ring-opening the furyl ring, formal [3 + 2] cycloaddition o-hydroxyphenyl group.

Язык: Английский

Процитировано

9