Note

FeCl₃-Catalyzed Cross-Dehydrogenative Coupling between Imidazoheterocycles and Oxoaldehydes

Sadhanendu Samanta^†, Susmita Mondal^†, Sougata Santra^‡, Golam Kibriya^†, and Alakananda Hajra^*^†

^† Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India

^‡ Department of Organic & Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Str., Yekaterinburg, 620002, Russian Federation

J. Org. Chem., 2016, 81 (20), pp 10088–10093

DOI: 10.1021/acs.joc.6b02091

Publication Date (Web): October 4, 2016

*E-mail: alakananda.hajra@visva-bharati.ac.in.

Abstract

An Fe(III)-catalyzed efficient dicarbonylation of imidazoheterocycles has been developed through cross-dehydrogenative coupling between imidazoheterocycles and oxoaldehydes under ambient air in high yields. The present protocol is also applicable to indolizines. Imidazopyridine produced bisimidazopyridine with arylaldehyde. Experimental results suggest that the reactions proceed through the nonradical pathway.

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.6b02091.

Scanned copies of ¹H and ¹³C NMR spectra of the synthesized compounds (PDF)
Crystallographic data for compound 5e (CIF)

View: ACS ActiveView PDF | PDF | PDF w/ Links | Full Text HTML

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

Palladium-catalyzed synthesis of indole fused coumarins via cross-dehydrogenative coupling

Amrita Dey, Md Ashif Ali, Sourav Jana, Sadhanendu Samanta, Alakananda Hajra

Tetrahedron Letters 2017 58 (4), 313-316

Related Content:

Synthesis of Quinazolines from N,N′-Disubstituted Amidines via I₂/KI-Mediated Oxidative C–C Bond Formation
The Journal of Organic Chemistry
Lv, Wang, Hu, Zhou, Yu, and Chang
2016 81 (20), pp 9924–9930

Abstract: An I₂/KI-promoted oxidative C–C bond formation reaction from C(sp³)–H and C(sp²)–H bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The required substrates are readily prepared from the corresponding acyl chlorides, ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
The Modern Face of Synthetic Heterocyclic Chemistry
The Journal of Organic Chemistry
Cabrele and Reiser
2016 81 (21), pp 10109–10125

Abstract: The synthesis of heterocycles is arguably one of the oldest and at the same time one of the youngest disciplines of organic chemistry. Groundbreaking principles to form heterocycles, mainly by condensation reactions, were recognized in the beginning of ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Cascade Reactions of Nitrones and Allenes for the Synthesis of Indole Derivatives
The Journal of Organic Chemistry
Anderson, Kroc, Reidl, and Son
2016 81 (20), pp 9521–9529

Abstract: Cascade reactions involving nitrones and allenes are known to facilitate the rapid synthesis of several indole derivatives. The chemoselectivity of these complicated transformations can be influenced by substrate functionalization, reaction conditions, ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions
Organic Letters
Chen, Li, Ni, Huang, and Deng
2016 18 (20), pp 5384–5387

Abstract: An efficient indole-to-carbazole strategy has been developed under metal-free conditions. This carbazole formation was highly promoted by NH₄I with high regioselectivity through formal [2 + 2 + 2] annulation of indoles, ketones, and nitroolefins. It thus ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Copper-Catalyzed Three-Component System for Arylsulfenylation of Imidazopyridines with Elemental Sulfur
The Journal of Organic Chemistry
Ravi, Reddy, Pappula, Samanta, and Adimurthy
2016 81 (20), pp 9964–9972

Abstract: A one-pot three-component reaction for the regioselective synthesis of thioarylated imidazoheterocycles from aryl halides and elemental sulfur using copper(I) iodide as a catalyst has been developed. Reactions proceed with high efficiency and afford ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Aerobic Copper-Catalyzed Halocyclization of Methyl N-Heteroaromatics with Aliphatic Amines: Access to Functionalized Imidazo-Fused N-Heterocycles
The Journal of Organic Chemistry
Tan, Zhao, Zhou, Jiang, and Zhang
2016 81 (20), pp 9939–9946

Abstract: A new aerobic copper-catalyzed halocyclization reaction of methyl N-heteroaromatics and aliphatic amines has been developed, which enables straightforward access to functionalized imidazo-fused N-heterocycles with the merits of good functional tolerance, ...

Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Dr.T の薬学コラム

2017年1月3日火曜日

Fe Mediated Oxidative Cross Copling 2017

Note

FeCl₃-Catalyzed Cross-Dehydrogenative Coupling between Imidazoheterocycles and Oxoaldehydes

Abstract

PDF

Crystallographic Information File

Palladium-catalyzed synthesis of indole fused coumarins via cross-dehydrogenative coupling

Other ACS content by these authors:

Related Content:

Metrics

0 件のコメント:

コメントを投稿

2017年1月3日火曜日

Fe Mediated Oxidative Cross Copling 2017

Note

FeCl3-Catalyzed Cross-Dehydrogenative Coupling between Imidazoheterocycles and Oxoaldehydes

Abstract

PDF

Crystallographic Information File

Palladium-catalyzed synthesis of indole fused coumarins via cross-dehydrogenative coupling

Other ACS content by these authors:

Related Content:

Metrics

Explore by:

0 件のコメント:

コメントを投稿

FeCl₃-Catalyzed Cross-Dehydrogenative Coupling between Imidazoheterocycles and Oxoaldehydes