3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides DOI Creative Commons
Jian‐Qiang Zhao, Wenjie Wang, Zhou Shun

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(14), P. 5529 - 5529

Published: July 20, 2023

An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as base, a wide range structurally diverse N-diarylmethylindole derivatives were obtained moderated to good yields via protection group migration/aza-1,6-Michael addition sequences. The reaction process also demonstrated by control experiments. Different from previous advances where 3-nitrodoles served electrophiles trapping various nucleophiles, herein is featured that defined latent N-centered nucleophiles react ortho-hydrophenyl p-QMs construction N-diarylmethylindoles.

Language: Английский

Umpolung α-regioselective 1,3-dipolar cycloaddition and internal recycle of byproduct as two key strategies: access to diverse chiral bipyridines DOI
Yu‐Heng Wang, Xirui Wang,

Ke‐Lan Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5428 - 5434

Published: Jan. 1, 2023

Herein, the first example of umpolung α-regioselective 1,3-dipolar cycloaddition optically pure perhydroindole-2-carboxylic acid 1a with pyridinecarboxaldehydes 2 is described.

Language: Английский

Citations

3
Fischer's base-triggered formal (3+2) cycloadditions with 3-isothiocyanato oxindoles as acceptor–donor synthons DOI
Xiong-Wei Liu,

Zi‐Yue Chen,

Ren-Ming Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(31), P. 4652 - 4655

Published: Jan. 1, 2023

Herein, previously unreported Fischer's base reactants serving as useful 2C building blocks in (3+2) cycloaddition reactions to build a library of bispiro[Fischer's base-oxindole] hybrids are described. These structurally intriguing products containing three adjacent quaternary stereocentres were smoothly afforded up 82% yield and >20 : 1 dr under catalyst-free conditions. Notably, the present protocol firstly employs 3-isothiocyanato oxindole an acceptor then donor formal cycloadditions, allowing practical, straightforward access diverse cycloadducts. This work expands applicability scope oxindoles, which have been limited behaving donor/acceptor-based synthons cycloadditions previous work.

Language: Английский

Citations

2
A regioselective [3 + 2] cycloaddition reaction of 2-benzylidene-1-indenones with functional olefins to access indanone-fused 2D/3D skeletons DOI

Yi-Hang Deng,

Chuan-Bao Zhang,

Jun-jie Sun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4388 - 4392

Published: Jan. 1, 2023

The regioselective [3 + 2] cycloaddition reaction of 2-benzylidene-1-indenones with functional olefins was established DABCO as a base under mild conditions. Using this approach, series diversely substituted indanone-fused cyclopentane polycycles highly crowded multiple substituents were synthesized in high yields.

Language: Английский

Citations

2
Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions DOI
Wenhui Zhang,

Zi‐Yue Chen,

Ren-Ming Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12296 - 12303

Published: Jan. 1, 2023

This is the first example of trimethylindolenines serving as useful C–N synthons in [3+2] cycloaddition reactions.

Language: Английский

Citations

1
3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides DOI Creative Commons
Jian‐Qiang Zhao, Wenjie Wang, Zhou Shun

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(14), P. 5529 - 5529

Published: July 20, 2023

An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as base, a wide range structurally diverse N-diarylmethylindole derivatives were obtained moderated to good yields via protection group migration/aza-1,6-Michael addition sequences. The reaction process also demonstrated by control experiments. Different from previous advances where 3-nitrodoles served electrophiles trapping various nucleophiles, herein is featured that defined latent N-centered nucleophiles react ortho-hydrophenyl p-QMs construction N-diarylmethylindoles.

Language: Английский

Citations

1