Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐heterocycles with N‐methoxyindoleamides and Isoxazolones DOI

Dan‐Ting Shen,

Wen‐Xuan Zou,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4089 - 4094

Published: July 20, 2024

Abstract A method for synthesizing pyrimido[ 1,2‐a ]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C−H activation/annulation strategy employing N ‐methoxyindoleamides and isoxazolones is developed. Also, framework of 3‐methoxy‐2,3‐dihydro‐[ 1,3,5 ]triazino[ ]indole‐4,10‐dione was successfully synthesized Cp*Rh‐catalyzed activation/annulation/oxidation reaction between N‐ (methyloxy)‐1 H ‐indole‐1‐carboxamide isoxazolones. These reactions demonstrated the suitability several substrates, compatibility with numerous functional groups, mild conditions. Preliminary mechanistic investigations have been completed.

Language: Английский

Modular Room Temperature Synthesis of Sulfoximidoyl Amidines Enabled by Pd-Catalyzed Cascade Aza-Claisen Rearrangement Strategy DOI
Huang Zhi-gang, Z. Y. Xu,

Tianming Huang

et al.

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

Published: Jan. 7, 2025

Reported herein is a concise synthesis of sulfoximidoyl amidines enabled by Pd-catalyzed cascade aza-Claisen rearrangement and nucleophilic reaction at room temperature. Free NH-sulfoximines N-allylynamides were employed as the modular building blocks to produce expected sulfoximine amidine derivatives in highly chemoselective models 100% atom efficiency. A broad range functional groups well tolerated under these gentle conditions give desired products generally good excellent yields.

Language: Английский

Citations

0
Pd-Catalyzed Regioselective Tandem Heck/C–H Activation/Bisamination Reactions with Ynamides and Diaziridinone. Rapid Access to 3-Aminoindoles DOI
Jianjun Wang, Wei Liu,

Jieling Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

This work describes a highly efficient Pd-catalyzed annulation process of aryl iodides, ynamides, and di-tert-butyldiaziridinone. A wide variety 3-aminoindoles bearing various functional groups have been readily obtained in up to 99% yield. 3-Aminoindole functionalities can also be easily introduced into medicinally important molecules. The reaction likely proceeds through sequential regioselective Heck C-H activation form pallada(II)cycle species, which is bisaminated with diaziridinone via pallada(IV)cycle intermediate. resulting serve as versatile precursors for the construction structurally diverse aza-polycyclic compounds.

Language: Английский

Citations

0
One-Pot Total Synthesis of Natural Products Nitramarine, Nitraridine, and Analogues via a Cascade Oxidation/Pictet–Spengler Condensation/Annulation Process DOI

Song Yingchun,

Wenhui Cao,

Ming‐Xuan Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12832 - 12841

Published: Aug. 9, 2024

A cascade oxidation/Pictet–Spengler condensation/annulation process has been developed for the one-pot total synthesis of nitramarine, nitraridine, and their analogues. The procedure proceeded with easily available quinolines tryptophan derivatives. simple metal-free approach, wide substrate scope, functional group tolerance make it applicable diverse bioactive Furthermore, bioactivity evaluation identified two promising leading compounds 5d 5e potent antitumor proliferative activity against breast cancer cells.

Language: Английский

Citations

3
Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel‐Mediated Cyclization of Tryptamine‐Ynamide DOI

Changhong Han,

Lu Yang,

K. YAO

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1355 - 1359

Published: Feb. 13, 2024

Comprehensive Summary An asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps (8 purifications) from L ‐tryptophan. The main feature our synthetic strategy is the efficient construction spirocyclic oxindole intermediate containing a chiral quaternary carbon center, involving silica gel‐mediated cyclization tryptamine‐ynamide and oxidation under neat conditions.

Language: Английский

Citations

1
Investigation of UV Light-Promoted Synthesis of α-Sulfonyl Amides from N-Sulfonyl Ynamides DOI

Aurélien Galibert-Guijarro,

Jérémy Tronc,

Dominique Mouysset

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9695 - 9699

Published: June 19, 2024

UV light-promoted synthesis of α-sulfonyl amides from N-sulfonyl ynamides without any additives is reported. The reaction proceeds through a radical chain mechanism involving the photoinduced cleavage nitrogen–sulfur bond and addition an electrophilic sulfonyl to triple ynamide followed by β-fragmentation group leading ketenimine hydrated upon workup. This highly efficient rearrangement leads, after acidic treatment, wide range in high yields.

Language: Английский

Citations

1
One-Pot Reaction Sequence: N-Acylation/Pictet–Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues DOI

Kseniya A. Alekseeva,

Milana A. Fedoseeva,

Olga Bakhanovich

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3065 - 3071

Published: Feb. 15, 2024

One-pot synthesis of tetrahydro-β-carbolines, fused with an isoindole core, was proposed starting from maleic anhydride and azomethines easily available tryptamines 3-(hetaryl)acroleins. This sequence includes four key steps: acylation the aldimine anhydride, a Pictet–Spengler cyclization, intramolecular Diels–Alder reaction, concluding [1,3]-H shift. As result, six- or seven-nuclear alkaloid-like heterocyclic systems, containing benzo[1,2]indolizino[8,7-b]indole fragment annulated furan, thiophene, pyrrole, are formed in diastereoselective manner.

Language: Английский

Citations

0
Access to Piperazine-Fused Pyrrolocarbazoles Enabled by Acid-Catalyzed Stereoselective Hydroarylation of Ynamide–Indoles and Subsequent Diels–Alder Reactions/Aromatizations DOI

Ze Zhou,

Xiang Huang,

Qingyi Wei

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7273 - 7278

Published: Aug. 12, 2024

Pyrrolocarbazole skeletons are well known to possess a variety of biological activities that might be therapeutically useful in the treatment cancers. Herein, an acid-catalyzed stereoselective hydroarylation/Diels–Alder cycloaddition/aromatization ynamide–indoles is described. We newly designed and synthesized piperazine-fused pyrrolocarbazole derivatives could further applied synthesis potent Wee1 inhibitors.

Language: Английский

Citations

0
Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐heterocycles with N‐methoxyindoleamides and Isoxazolones DOI

Dan‐Ting Shen,

Wen‐Xuan Zou,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4089 - 4094

Published: July 20, 2024

Abstract A method for synthesizing pyrimido[ 1,2‐a ]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C−H activation/annulation strategy employing N ‐methoxyindoleamides and isoxazolones is developed. Also, framework of 3‐methoxy‐2,3‐dihydro‐[ 1,3,5 ]triazino[ ]indole‐4,10‐dione was successfully synthesized Cp*Rh‐catalyzed activation/annulation/oxidation reaction between N‐ (methyloxy)‐1 H ‐indole‐1‐carboxamide isoxazolones. These reactions demonstrated the suitability several substrates, compatibility with numerous functional groups, mild conditions. Preliminary mechanistic investigations have been completed.

Language: Английский

Citations

0