Construction of Spiropyrroloindolines by Dearomative [3+2]-Cycloaddition of Indoles with Oxindole-Embedded Azaoxyallyl ­Cations DOI
Jaideep Saha, Bandana Singh,

Tishyasoumya Bera

et al.

Synlett, Journal Year: 2022, Volume and Issue: 34(05), P. 465 - 470

Published: July 25, 2022

Abstract A dearomative [3+2]-cycloaddition reaction of oxindole-embedded azaoxyallyl cations with indoles at the C3 position has been developed. The use this new class cation species in permits access to more-elaborate hexahydropyrrolo[2,3-b]indole moieties that contain a spiro-oxindole ring. transformation displays broad substrate scope and good regio- stereoselectivity for cycloaddition step. Several observations suggested can display different reactivity pattern from those commonly employed systems.

Language: Английский

Electrochemically driven α-thiocarbamylation via a dehydrocoupling strategy of β-ketoesters with amines and CS2 DOI
Qian Wang, Xiu‐Jin Meng, Haitao Tang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2572 - 2576

Published: Jan. 1, 2023

We disclose a feasible strategy for the electrochemical dehydrogenative coupling of CS 2 and amines with β-ketoesters, which leads to dithiocarbamate intermediates in presence bases.

Language: Английский

Citations

19

Catalyst- and additive-free syntheses of rhodanine andS-alkyl dithiocarbamate derivatives from sulfoxonium ylides DOI
Ajay Sharma, Satyendra Kumar Pandey

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(11), P. 1509 - 1512

Published: Jan. 1, 2023

An efficient catalyst- and additive-free facile access to rhodanine S -alkyl dithiocarbamate derivatives via multi-component reaction of amines, CS 2 α-ester sulfoxonium ylides in methanol has been described.

Language: Английский

Citations

10

Bis(dialkylaminethiocarbonyl)disulfides Act as Electron Acceptors for EDA Complexes for the Synthesis of Dithiocarbamate Derivatives under Visible Light DOI
Hong Yang, Yuanyuan Cheng, Haibo Zhu

et al.

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

Published: Jan. 14, 2025

This study proposes a green and efficient atom- step-economical method for converting hazardous CS2 to dithiocarbamate derivatives under visible light irradiation catalyst-free conditions. By the construction of novel C-S C-N bonds, series β-dicarbonyl compounds amines are incorporated into products. Under light, amine first form bis(dialkylaminethiocarbonyl)disulfides, which then react with K2CO3-activated electron donor-acceptor (EDA) complexes subsequently generate target confirms time that bis(dialkylaminethiocarbonyl)disulfides can act as acceptors an EDA complex compounds, coupled product light.

Language: Английский

Citations

0

Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2 DOI
Peng‐Fei Huang, Ying Peng,

Jia-Le Fu

et al.

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

Published: March 29, 2025

1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report green electrochemical three-component reaction amines, amidines, and CS2 for the effective synthesis 3,5-disubstituted-1,2,4-thiadiazoles under metal- oxidant-free conditions. Both aliphatic aryl amines well-tolerated at room temperature simple undivided cell. A series 1,2,4-thiadiazoles prepared with excellent functional groups.

Language: Английский

Citations

0

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions DOI

Deeksha,

Ritesh Singh

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(47)

Published: Oct. 10, 2022

Abstract Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively a 3‐unit synthon 1,3 dipoles create N‐heterocycles via cycloaddition reactions, wherein cation served electrophilic counterpart. Recently, new variations been reported, including usage 1,4 dipole domino and unique alkylating ability heteroatoms. This review article provides an update recent developments this area prevailing mechanistic insight.

Language: Английский

Citations

9

Metal‐Free Synthesis of 2‐Aminobenzothiazoles via I2‐Catalyzed Tandem Cyclization Reaction of Amines and Carbon Disulfide DOI
Ting Chen, Wei Feng, Ruitong Yang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(8), P. 846 - 852

Published: Dec. 20, 2023

Comprehensive Summary A convenient approach for the construction of 2‐aminobenzothiazoles via I 2 ‐catalyzed tandem cyclization reaction amines and carbon disulfide has been developed. The present starts from simple readily available starting materials, affording a series in up to 89% yields under metal‐free conditions. In this work, C—H/N—H functionalization was achieved multiple C‐hetero bonds were successfully constructed one pot.

Language: Английский

Citations

5

Access to 3,3′-disubstituted peroxyoxindole derivatives and α-peroxyamides via azaoxyallyl cation-guided addition of hydroperoxides DOI

Tishyasoumya Bera,

Bandana Singh, Manoranjan Jana

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(54), P. 7538 - 7541

Published: Jan. 1, 2022

Herein, a transition metal-free approach for access to 3,3'-disubstituted peroxyoxindole is disclosed, which harnesses transient azaoxyallyl cation. This strategy also applicable the synthesis of structurally diverse α-peroxycarboxylic acid surrogates. The method exhibits good functional group tolerance and suitable generating library peroxy-containing compounds.

Language: Английский

Citations

8

A concise approach to 2-pyrrolin-5-one scaffold construction from α-halohydroxamates and β-keto compounds DOI
Wenjie Lan, Xuan Yu, Mengzhu Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(37), P. 7535 - 7540

Published: Jan. 1, 2023

A concise approach to the construction of 2-pyrrolin-5-one scaffold was developed via a one-pot reaction with formal [3 + 2] annulation/elimination between β-keto nitrile/β-keto ester and unsubstituted α-halohydroxamates.

Language: Английский

Citations

4

Metal-Free One-Pot Domino Synthesis of Oxazolidinethione Derivatives of Quaternary Amino Acids from α-Amino Esters and Aldehydes Using CS2 DOI
Dinesh R. Shinde, Gamidi Rama Krishna, Udaya Kiran Marelli

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7109 - 7114

Published: Feb. 6, 2024

We present a streamlined, metal-free, one-pot domino approach to efficiently synthesize oxazolidinethione derivatives containing substituted quaternary amino acids. This method employs α-amino esters, aldehydes, and CS2 under mild conditions, constructing three new bonds (C–N, C–C, C–O) produce compounds featuring center beta-hydroxy derivative in high yields. scalable protocol enables the creation of libraries biologically significant, intricate acid using esters aldehydes.

Language: Английский

Citations

1

Photoinduced Deconstructive Alkylation Approach Enabled by Oxy-Radicals from Alcohols DOI

Yiman Gao,

Yan Li,

W. B. Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Alcohols are the most commercially abundant, synthetically versatile and operationally convenient functional groups in organic chemistry. Therefore, a strategy that utilizes hydroxy-containing compounds to develop novel bond disconnection formation process would achieve molecular diversity. Herein, deconstructive for generation of quinoxalin-2(1H)-one derivatives has been developed from alcohol precursors via oxy-radical-induced β-fragmentation. Additionally, 1,5-HAT deoxygenation by P(III) along with oxy-radical were demonstrated as alternative pathways this transformation. Furthermore, deep-seated reorganization few terpenes carbon framework, unique activity inhibition against growth pathogenic fungi was observed.

Language: Английский

Citations

1