Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a ruthenium-catalyzed hydrogen transfer strategy

Xie, Feng; Zhang, Min; Jiang, Huanfeng; Chen, Mengmeng; Lv, Wan; Zheng, Aibin; Jian, Xiujuan

doi:10.1039/c4gc01316f

Cited by 87 publications

(35 citation statements)

References 70 publications

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“…The scope of the present catalytic system is also extended for the preparation of quinoxalines, a class of N ‐heterocyclic compounds which were extensively studied due to their broad range of biological properties and their applications in pharmaceutical as well as agrochemical arenas . Jian and co‐workers described various routes to access the quinoxaline motif . To overcome the difficulty of handling various starting materials, focus towards the development of a simple catalytic system for the preparation of quinoxalines is essential.…”

Section: Introductionmentioning

confidence: 84%

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

et al. 2019

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Three copper(I) complexes, [CuCl(L)(PPh 3 ) 2 ] [L = FL (1), BL (2) or TL (3)] were prepared from [(PPh 3 ) 2 Cu-(μ-Cl) 2 Cu(PPh 3 )] and N-carbamothioylfuran-2-carboxamide (FL), N-carbamothioylbenzamide (BL) or N-carbamothioylthiophene-2-carboxamide (TL) ligands in benzene and four-coordinated tetrahedral copper complexes were well characterized by various spectroscopic techniques (UV/Vis, FT-IR, 1 H NMR, 13 C NMR and 31 P NMR). The molecular structure of the ligands (FL and BL) and complexes was established from single-crystal X-ray diffraction studies. Copper complexes have been shown to cata- [a]

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Section: Introductionmentioning

confidence: 84%

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

et al. 2019

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“…Optimization studies reveal that [Ru 3 (CO) 12 ] in combination with dppp served as an active catalyst in the presence of 50 mol % CsOH⋅H 2 O in t ‐amyl alcohol at 150 °C. Both symmetrical and unsymmetrical diol derivatives were converted into the corresponding 2,3‐substituted quinoxaline derivatives ( 48 ) and electron‐donating and electron‐withdrawing substituents on anilines significantly influenced the product yield 9e …”

Section: Synthesis Of N‐heterocyclesmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Hydrogen‐Transfer Annulations: Access to Heterocyclic Scaffolds

et al. 2015

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The ability of hydrogen-transfer transition-metal catalysts, which enable increasingly rapid access to important structural scaffolds from simple starting materials, has led to a plethora of research efforts on the construction of heterocyclic scaffolds. Transition-metal-catalyzed hydrogen-transfer annulations are environmentally benign and highly atom-economical as they release of water and hydrogen as by-product and utilize renewable feedstock alcohols as starting materials. Recent advances in this field with respect to the annulations of alcohols with various nucleophilic partners, thus leading to the formation of heterocyclic scaffolds, are highlighted herein.

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“…In Optimierungsstudien erwies sich [Ru 3 (CO) 12 ] in Kombination mit dppp als aktiver Katalysator, wenn in Gegenwart von 50 Mol‐% CsOH⋅H 2 O in tert ‐Amylalkohol auf 150 °C erhitzt wurde. Symmetrische und unsymmetrische Diolderivate wurden in die entsprechenden 2,3‐substituierten Chinoxalinderivate 48 umgesetzt, und sowohl elektronenschiebende als auch elektronenziehende Substituenten an den Anilinen hatten einen signifikanten Einfluss auf die Produktausbeute 9e …”

Section: Synthese Von N‐heterocyclenunclassified

Übergangsmetallkatalysierte Wasserstofftransferanellierungen: Zugang zu heterocyclischen Gerüsten

et al. 2015

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Übergangsmetall‐Wasserstofftransferkatalysatoren ermöglichen ausgehend von einfachen Ausgangsmaterialien einen schnellen Zugang zu wichtigen Strukturmotiven, so auch zu Heterocyclen. Übergangsmetallkatalysierte Wasserstofftransferanellierungen sind umweltverträglich und in hohem Maße atomökonomisch, da sie Wasser und Wasserstoff als Nebenprodukt freisetzen und erneuerbare Alkohole als Ausgangsmaterialien verwenden. Hier werden neueste Fortschritte auf diesem Gebiet im Hinblick auf Anellierungen von Alkoholen mit verschiedenen nucleophilen Reaktionspartnern vorgestellt, bei denen heterocyclische Gerüste gebildet werden.

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Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a ruthenium-catalyzed hydrogen transfer strategy

Abstract: An efficient synthesis of quinoxalines from 2-nitroanilines and biomass-derived vicinal diols is demonstrated via a hydrogen transfer strategy.

Cited by 87 publications

References 70 publications

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

Transition‐Metal‐Catalyzed Hydrogen‐Transfer Annulations: Access to Heterocyclic Scaffolds

Übergangsmetallkatalysierte Wasserstofftransferanellierungen: Zugang zu heterocyclischen Gerüsten

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