A Chromium Catalytic System for the Synthesis of Aryl‐Substituted 1,3,5‐Triazines and Pyrimidines by Acceptorless Dehydrogenative Coupling DOI

Baojin Feng,

Wantong Yue,

Dongyue Wei

et al.

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

Published: Oct. 19, 2024

Abstract A novel and highly efficient method for the synthesis of 2,4,6‐triaryl‐1,3,5‐triazines 2,4,6‐trisubstituted pyrimidines from amidines alcohols has been established. Using an Earth‐abundant air‐stable chromium salt catalyst a phosphine‐free ligand, developed Cr‐catalyzed acceptorless dehydrogenative coupling provides 1,3,5‐triazines with high yields good functional group tolerance. Moreover, synthetic value this operationally simple protocol was demonstrated by gram‐scale experiment linker to construct various supramolecular complexes.

Language: Английский

Recent advances in sustainable synthesis of N-heterocycles following acceptorless dehydrogenative coupling protocol using alcohols DOI
Milan Maji, Dibyajyoti Panja, Ishani Borthakur

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(11), P. 2673 - 2709

Published: Jan. 1, 2021

In this review, we have summarized various aspects of homogeneous and heterogeneously catalyzed recent advancements in the synthesis heterocycles following ADC approach.

Language: Английский

Citations

144

Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines DOI
Ankur Maji, Shivangi Gupta, Milan Maji

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8351 - 8367

Published: June 21, 2022

Herein, we report a simple, phosphine-free, and inexpensive catalytic system based on manganese(II) complex for synthesizing different important N-heterocycles such as quinolines, pyrroles, pyridines from amino alcohols ketones. Several control experiments, kinetic studies, DFT calculations were carried out to support the plausible reaction mechanism. We also detected two potential intermediates in cycle using ESI-MS analysis. Based these metal-ligand cooperative mechanism was proposed.

Language: Английский

Citations

41

Dehydrogenative Synthesis of Quinolines and Quinazolines via Ligand-Free Cobalt-Catalyzed Cyclization of 2-Aminoaryl Alcohols with Ketones or Nitriles DOI
Zhiqiang Hao, Xiaoyu Zhou, Zongwen Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12596 - 12607

Published: Sept. 26, 2022

We present a convenient and efficient protocol to synthesize quinolines quinazolines in one pot under mild conditions. A variety of substituted were synthesized good excellent yields (up 97% yield) from the dehydrogenative cyclizations 2-aminoaryl alcohols ketones catalyzed by readily available Co(OAc)2·4H2O. This cobalt catalytic system also showed high activity reactions 2-aminobenzyl with nitriles, affording various quinazoline derivatives 95% yield). The offers an environmentally benign approach for synthesis N-heterocycles employing earth-abundant salt ligand-free

Language: Английский

Citations

38

Ruthenium pincer complex catalyzed efficient synthesis of quinoline, 2-styrylquinoline and quinazoline derivatives via acceptorless dehydrogenative coupling reactions DOI

Dipanjan Bhattacharyya,

Priyanka Adhikari,

Kritartha Deori

et al.

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(18), P. 5695 - 5702

Published: Jan. 1, 2022

The synthesis of N-heterocycles has been considered an emerging area chemical research due to their extensive utilization in pharmaceuticals, materials science, and natural product synthesis.

Language: Английский

Citations

36

Historical perspective on ruthenium-catalyzed hydrogen transfer and survey of enantioselective hydrogen auto-transfer processes for the conversion of lower alcohols to higher alcohols DOI Creative Commons
Eliezer Ortiz, Jonathan Z. Shezaf, Weijia Shen

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(43), P. 12625 - 12633

Published: Jan. 1, 2022

Ruthenium-catalyzed hydrogen auto-transfer reactions for the direct enantioselective conversion of lower alcohols to higher are surveyed. A brief historical perspective on ruthenium-catalyzed transfer is given.

Language: Английский

Citations

26

Well‐Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α‐Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines DOI
Rahul Sharma, Avijit Mondal,

Arup Samanta

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(14), P. 2429 - 2437

Published: May 23, 2022

Abstract The “borrowing hydrogen” (BH) method for C‐alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst borrowing hydrogen transformation a key challenge to be witnessed. Herein we have presented synthesis of non‐phosphine, easily accessible SNS−Ni complexes. Ni‐catalyst was successfully applied the ketone enolates α‐alkylated ketones. Primary with different functional groups various heteroaromatic alcohols are well tolerated. present system efficiently gram scale also green chemistry metrics reaction were calculated. protocol extended biologically quinoline moieties. Finally, control experiments deuterium labelled suggest that proceeds via pathway. magnified image

Language: Английский

Citations

24

Arene Binuclear Ru(II)-Promoted Sustainable Synthesis of Substituted Pyrazoles from Alcohols via Acceptorless Dehydrogenative Annulation DOI
Veerappan Tamilthendral, Rengan Ramesh

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4162 - 4167

Published: May 31, 2023

We report a selective and sustainable synthesis of substituted pyrazoles via an eco-friendly acceptorless dehydrogenative annulation (ADA) greener alcohols, malononitrile, various aromatic hydrazides by newly synthesized binuclear Ru(II) p-cymene complexes. A discrete set complexes are fabricated structurally characterized analytical, spectral, single-crystal X-ray diffraction methods. Further, the catalytic effectiveness is explored for construction 5-amino-4-cyano-N-aroylpyrazoles (34 examples) under mild conditions produces H2O/H2 as only byproduct. sequence polysubstituted has been constructed in 62-95% yield using 1 mol % catalyst loading. Probable intermediates detected reaction have isolated confirmed nuclear magnetic resonance electrospray ionization mass spectrometry studies. Expediently, therapeutically significant gout medicine "allopurinol" analogue derived successfully from 5-amino-4-cyano-N-aroylpyrazoles.

Language: Английский

Citations

13

Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles DOI
Fatemeh Doraghi,

Farzad Gilaninezhad,

Somaye Karimian

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

Citations

4

Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles DOI
Shiqi Zhang, Ji‐Bao Xia

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2613 - 2623

Published: Jan. 1, 2024

A Ru-catalyzed selective hydroacylation of acrylonitriles with aldehydes or alcohols towards β-ketonitriles is established. Glutaronitriles can be obtained through a one-step tandem and Michael addition acrylonitrile alcohols.

Language: Английский

Citations

3

Temperature-dependent switchable synthesis of imines and amines via coupling of alcohols and amines using pyrrolyl-imine ruthenium catalysts DOI
Qing Li, Yu Hou,

Mengxuan Bai

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 115895 - 115895

Published: Dec. 1, 2024

Language: Английский

Citations

3