Synthesis of Poly‐Substituted Pyridines via Noble‐Metal‐Free Cycloaddition of Ketones and Imines DOI

Yeting Mao,

Hong Mao,

Jiaojiao Xu

et al.

Chemistry - An Asian Journal, Journal Year: 2021, Volume and Issue: 16(23), P. 3905 - 3908

Published: Oct. 9, 2021

An eco-friendly and noble-metal-free formal [4+2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones imines, whereby two sequential C-C bonds are formed. The given approach features a unique synthetic strategy imines with wide substrate scope, good functional group tolerance, mild conditions operational simplicity, which represents more direct pathway to synthesize than traditional methods.

Language: Английский

Unmasking the reverse reactivity of cyclic N-sulfonyl ketimines: multifaceted applications in organic synthesis DOI
Soumitra Guin, Debashis Majee, Sampak Samanta

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(72), P. 9010 - 9028

Published: Jan. 1, 2021

This feature article covers the recent status on reactivities of α-alkyl cyclic N -sulfonyl ketimines as resourceful nucleophiles, targeting fused carbo- and heterocycles, aza-arenes etc . In addition, mechanistic studies have been presented.

Language: Английский

Citations

35

Base-Promoted and Copper(I)-Catalyzed Tandem Cyclization-C(sp2)-N Coupling of Vinyl Malononitriles with Ortho-Nitrochalcones: Access to Acridones and their Fused Derivatives DOI

Raju Lal Dhakar,

S Banuprakash Goud,

Sampak Samanta

et al.

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

Published: Feb. 28, 2025

An efficient Cs2CO3-promoted and copper(I)-catalyzed double cyclization of ortho-nitrochalcones with vinyl malononitriles for the de novo access to a variety tri- tetra-substituted acridones their fused derivatives value-added CN group has been developed first time. This one-pot operation proceeds through Michael-cyclization-aromatization, followed by regioselective ipso-amination via nucleophilic aromatic substitution (SNAr) reaction, resulting in two C═C bonds C-N bond acridone ring synthesis. economic strategy based on 100% carbon atoms ensures successive formation rings operation, good high yields, wide range substrates, tolerance functionalities. In addition, were converted into several acridines, highlighting synthetic versatility usefulness prepared derivatives.

Language: Английский

Citations

0

1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines DOI
Soumitra Guin, Santosh K. Gudimella, Sampak Samanta

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(7), P. 1337 - 1342

Published: Jan. 1, 2020

A base-promoted 1,6-addition–cyclization reaction of vinyl para-quinone methides with cyclic sulfamidate imines in an open atmosphere is reported. This method delivers good to high yields 2,4,6-trisubstituted pyridines a valuable phenolic moiety at the C4-position.

Language: Английский

Citations

21

The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process DOI

Kejin Yuan,

Feng‐Ying Dong, Xiangcong Yin

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(23), P. 3868 - 3873

Published: Jan. 1, 2020

The dual alkylation of the C(sp3)–H bond cyclic α-methyl-N-sulfonyl imine has been achieved through piperidine-promoted cascade condensation/[1,5]-hydride transfer/cyclization from and o-aminobenzaldehyde in trifluoroethanol.

Language: Английский

Citations

20

Recent advances and future challenges in the synthesis of 2,4,6-triarylpyridines DOI
Dmitrii A. Shabalin

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(38), P. 8184 - 8204

Published: Jan. 1, 2021

The present review is focused on recent advances (2015–present) in the synthesis of 2,4,6-triarylpyridines (also known as Kröhnke pyridines).

Language: Английский

Citations

17

Organocatalyzed diastereoselective cyclization of β-alkyl nitroolefins with alkylidene malononitriles: new approach to azetidine nitrones and isoxazoles DOI

Shikha Singh Rathor,

Ashvani K. Patel, Sampak Samanta

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1782 - 1789

Published: Jan. 1, 2024

An organocatalytic domino reaction of β-alkyl nitroolefins with alkylidene malononitriles to give azetidine nitrones good diastereoselectivities is reported. The in situ -generated were transmuted into isoxazoles catalyzed by acid.

Language: Английский

Citations

2

One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system DOI

Rajni Lodhi,

S Banuprakash Goud,

Sampak Samanta

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14163 - 14169

Published: Jan. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Language: Английский

Citations

2

An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates DOI
Екатерина Е. Галенко, Mariya A. Kryukova, Михаил С. Новиков

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(9), P. 6888 - 6896

Published: April 13, 2021

A four-step quasi one-pot procedure for the preparation of fully substituted nicotinates from ketone enamines and 4-methylideneisoxazol-5-ones has been developed. The reaction sequence involves (1) with formation isoxazole-5-ols, (2) their O-methylation diazomethane, (3) hydrogenative cleavage O–N bond in 5-methoxyisoxazoles under action Mo(CO)6/H2O simultaneous isomerization condensation formed enamines, dihydropyridines, (4) aromatization latter.

Language: Английский

Citations

15

Sustainable Four-Component Annulation for the Synthesis of 2,3,4,6-Tetraarylpyridines DOI

Yuxin Ding,

Renchao Ma,

Xu‐Qiong Xiao

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(5), P. 3897 - 3906

Published: Feb. 17, 2021

A one-pot, four-component annulation of 2,3,4,6-tetraarylpyridines from aromatic aldehydes, methyl ketones, diaryl ethanones, and ammonium acetate is described. The reaction features high functional group compatibility in air under solvent-free conditions without any additive only water as the nontoxic byproduct, providing a strategy for facile, economical, eco-friendly construction multiaryl-substituted pyridines simple readily available reactants.

Language: Английский

Citations

14

An organophotoredox-catalyzed C(sp2)–N cross coupling reaction of cyclic aldimines with cyclic aliphatic amines DOI
Xue Liu, Jingjing Wang, Ziyan Wu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(16), P. 3595 - 3600

Published: Jan. 1, 2021

An organophotocatalyzed C(sp2)-H/N-H cross-dehydrogenative coupling of cyclic aldimines with aliphatic amines has been developed, which represents the first example visible-light-induced C-H amination N-sulfonylated imines. This methodology enables streamline assembly amine derivatives via radical mediated C-N bond formation. The current protocol features transition-metal-free, mild conditions, good functional group tolerance and yields.

Language: Английский

Citations

12