Gallium (III) Triflate-Catalyzed Synthesis of Heterocycles: Quinoxalines, 1,5-Benzodiazepines and Their Fluorinated Derivatives

Prakash, GK Surya; Vaghoo, Habiba; Venkat, Arthi; Panja, Chiradeep; Chacko, Sujith; Mathew, Thomas; Oláh, George A.

doi:10.4155/fmc.09.77

Cited by 13 publications

(7 citation statements)

References 43 publications

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“…The strong and robust Lewis acid organometallics Ga(C 6 F 5 ) 3 , readily accessible from GaCl 3 and Zn(C 6 F 5 ) 2 (26), was recently used as olefin polymerization initiator. For instance, Ga(C 6 F 5 ) 3 effectively polymerizes styrene for the production of medium-to-high molecular weight polystyrene (PS, M w = 26.05 kg mol −1 , PDI = 2.4) in aqueous solution.…”

Section: Tris(pentafluorophenyl)galliummentioning

confidence: 99%

Gallium and Indium Compounds in Homogeneous Catalysis

Dagorne

Fliedel

Frémont

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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The present contribution highlights the most recent and representative developments on the use of Ga and In species in homogeneous catalysis. Recent studies of various ligand‐supported Ga(III) and In(III) compounds in cyclic esters polymerization catalysis for the production of biodegradable polyester materials are also included. Various organic transformations may now be catalyzed using Ga(III) and In(III) Lewis acids allowing access to a wide range of valuable organic molecules through diverse reaction sequences. The recent use of stable and robust N ‐heterocyclic carbene Ga(III) and In(III) compounds as strong π‐Lewis acid catalysts for various organic reactions is also discussed: such species are certainly promising for the future developments of Ga(III)‐ and In(III)‐mediated reactions. Although Lewis acid‐assisted reactions certainly dominate the field in Ga(III) and In(III) chemistry, discrete low‐valent In(I) species, presently emerging in catalysis, clearly display a distinct reactivity allowing their exploitation both as soft Lewis acids and alkyl‐/allyl‐/arylating agents.

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Section: Tris(pentafluorophenyl)galliummentioning

confidence: 99%

Gallium and Indium Compounds in Homogeneous Catalysis

Dagorne

Fliedel

Frémont

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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“…Several methods for the synthesis of 1,2‐dihydroquinoxalin‐2(1 H )‐ones have been reported in the literature, and among these, the Hinsberg reaction is a straightforward high yielding method that involves the heterocyclization of o ‐phenylenediamine with α ‐ketoesters in the presence of a catalyst such as acetic acid , sulfuric acid , citric acid , gallium triflate , and polyaniline sulfate salt . The general applicability of catalyst for different alkyl/aryl/heteroaryl α ‐ketoesters substrates remains doubtful, and thus, synthesizing novel heterocyclic quinoxalin‐2(1 H )‐ones via Hinsberg reaction remains a challenging task.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Expedite Synthesis of 2‐Phenylimidazo[1,2‐a]pyridylquinoxalin‐2(1H)‐ones

Sakhuja

Shakoor

Kumari

et al. 2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).An efficient methodology has been developed for the synthesis of quinoxalin-2(1H)-one derivatives of 2phenylimidazo[1,2-a]pyridines by microwave-irradiated Hinsberg heterocyclization between 2-phenylimidazo [1,2-a]pyridine-3-glyoxalates and o-phenylenediamine using either montmorillonite K-10 or Yb(OTf) 3 as catalysts. Montmorillonite K-10 was proven to be an efficient catalyst for the heterocyclization reaction between sterically hindered glyoxalate and o-phenylenediamine only under microwave conditions. The use of Yb(OTf) 3 /tetrahydrofuran was also found to be an effective catalyst for the above chemical transformation among a series of Lewis acids screened under microwave conditions; however, comparatively lesser yields were obtained as compared with the use of montmorillonite K-10.

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“…Although a number of methods for the synthesis of 1,5‐benzodiazepines have been reported,8 owing to their immense utility in the field of medicinal chemistry, the development of more efficient routes for their synthesis, as well as for the construction of new 1,5‐benzodiazepine‐based molecules, remains an active research field 10–12. With this in mind, in this paper, we disclose a versatile method for the synthesis of a new class of pyrano‐fused 1,5‐benzodiazepines.…”

Section: Introductionmentioning

confidence: 99%

Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination

2013

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Sugar‐based Morita–Baylis–Hillman (MBH) acetates easily obtained from commercially available D‐glucal underwent rapid reaction with 1,2‐benzenediamines to give, in good yields, a series of enantiomerically pure tricyclic pyrano‐fused 1,5‐benzodiazepines with multiple points of diversity, which could serve as potential drug scaffolds. The driving force behind this reaction seemed to be the high stability associated with the conjugated tricyclic system. The reaction involved an unprecedented amine–carbonyl condensation/[3,3]‐sigmatropic rearrangement/cyclization cascade.

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Gallium (III) Triflate-Catalyzed Synthesis of Heterocycles: Quinoxalines, 1,5-Benzodiazepines and Their Fluorinated Derivatives

Abstract: Quinoxalines, benzodiazepines and their fluorinated derivatives have been prepared in excellent yields from the corresponding diamines and diketones using gallium (III) triflate as an efficient and environmentally friendly catalyst, due to its stability, recyclability and minimal toxicity.

Cited by 13 publications

References 43 publications

Gallium and Indium Compounds in Homogeneous Catalysis

Gallium and Indium Compounds in Homogeneous Catalysis

Microwave‐Assisted Expedite Synthesis of 2‐Phenylimidazo[1,2‐a]pyridylquinoxalin‐2(1H)‐ones

Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination

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