Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones DOI

Lingyun Zhu,

Jing Sun,

Dan Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(47), С. 9392 - 9397

Опубликована: Янв. 1, 2023

An iodine-promoted domino reaction of arylamines/benzylamines, dialkyl but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones showed very interesting molecular diversity. The in acetonitrile at 65 °C the presence 30% mmol I2 resulted spiro[indoline-3,1'-pyrido[4,3-b]indoles] satisfactory yields. When anilines without para-substituents were used reaction, a direct substitution hydroxyl group to 2-(phenylamino)maleate para-position aniline gave chain products good Additionally, similar reactions with benzylamines not only spiro[indoline-3,1'-pyrido[4,3-b]indoles], but also afforded spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones lower A plausible annulation mechanism was rationally proposed for formation different kinds polycyclic compounds.

Язык: Английский

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
Selective construction of polycyclic cyclohepta[b]indoles and cyclopenta[b]indoles via cycloaddition reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)methanols DOI

Jing Sun,

Yan Chen, Qiu Sun

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(14), С. 6694 - 6699

Опубликована: Янв. 1, 2023

The polycyclic cyclohepta[ b ]indoles were efficiently obtained via a formal [4+3] cycloaddition and an unprecedented rearrangement of the maleimide motif from C3/C2-position indole ring.

Язык: Английский

Процитировано

7
Molecular Diversity of Base Promoted Annulation of MBH Carbonates of Isatins and Dialkyl But‐2‐ynedioates DOI Open Access
Ting Tang, Xueyan Liu,

Jing Sun

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(39)

Опубликована: Окт. 19, 2023

Abstract DABCO promoted one‐pot three‐component reaction of aromatic amines, dialkyl but‐2‐ynedioates and MBH nitriles isatins selectively afforded two diastereomeric spiro[indoline‐3,4′‐pyridines] in comparable yields. On the other hand, cyclization carbonates DCM at room temperature gave spiro[cyclopentane‐1,3′‐indoline] derivatives, while chloroform 70 °C resulted unique cyclopenta[ c ]quinolone derivatives with ring‐opening isatin moiety. A plausible mechanism was rationally proposed to explain formation different products.

Язык: Английский

Процитировано

4
DBU‐Catalyzed Vinylogous Reaction of 3‐Cyano‐4‐methylcoumarins with 3‐Arylsulfonyl‐3‐indolyloxindoles DOI Open Access

Mritunjay Mritunjay,

Shubham Sharma, Pushpinder Singh

и другие.

ChemistrySelect, Год журнала: 2024, Номер 9(30)

Опубликована: Авг. 6, 2024

Abstract An efficient metal‐free DBU catalyzed approach for the construction of biologically significant quaternary carbon centered C‐3 functionalized 2‐oxindole derivatives through vinylogous reaction 3‐cyano‐4‐methylcoumarins with 3‐arylsulfonyl‐3‐indolyloxindoles has been developed first time. The protocol is simple, cost‐effective, and producing desired products in good yields, without utilizing potentially harmful chemicals. Moreover, synthesized 3,3‐disubstituted molecules contain established pharmacophors their structure, i. e ., oxindole‐, indole‐ coumarin‐ moieties, which makes them a valuable candidate drug development process.

Язык: Английский

Процитировано

1
Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones DOI

Lingyun Zhu,

Jing Sun,

Dan Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(47), С. 9392 - 9397

Опубликована: Янв. 1, 2023

An iodine-promoted domino reaction of arylamines/benzylamines, dialkyl but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones showed very interesting molecular diversity. The in acetonitrile at 65 °C the presence 30% mmol I2 resulted spiro[indoline-3,1'-pyrido[4,3-b]indoles] satisfactory yields. When anilines without para-substituents were used reaction, a direct substitution hydroxyl group to 2-(phenylamino)maleate para-position aniline gave chain products good Additionally, similar reactions with benzylamines not only spiro[indoline-3,1'-pyrido[4,3-b]indoles], but also afforded spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones lower A plausible annulation mechanism was rationally proposed for formation different kinds polycyclic compounds.

Язык: Английский

Процитировано

3