Indium trichloride catalyzed regioselective synthesis of substituted pyrroles in water

Suresh, R.; Muthusubramanian, Shanmugam; Nagaraj, Muthupandi; Manickam, Govindaswamy

doi:10.1016/j.tetlet.2012.11.065

Cited by 44 publications

(21 citation statements)

References 53 publications

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“…We have already described the synthetic utility of a-azido chalcones 1 in generating heterocyclic compounds. [13] b-Hydroxyarylethanamide 2, derived from the chalcones 1, have also been exploited by us to construct new rings [14] and it has been shown that the nature of the acid employed has emphatically dictated the course of cyclization. Thus titatinum tetrachloride-catalyzed cyclization has led to isoxazolines 3 [ Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Isoquinoline Derivatives from β-Hydroxyarylethanamides

Suresh

Muthusubramanian

2015

Synthetic Communications

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A simple and efficient protocol for the construction of medicinally important substituted isoquinolines through intramolecular cyclization of b-hydroxyarylethanamides using acetic anhydride and phosphorous pentoxide in dioxane has been described. The chemo-and regioselectivities due to the influence of different catalysts were investigated and optimized for good to excellent yields. All the synthesized compounds have been characterized by NMR and mass spectral analyses.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Isoquinoline Derivatives from β-Hydroxyarylethanamides

Suresh

Muthusubramanian

2015

Synthetic Communications

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“…66 The reaction proceeds by denitrogenative decomposition of the α-azido chalcone to form a highly strained 2H-aziridine, which undergoes a nucleophilic attack from the diketone. Heck Coupling: Synthesis of Internal Alkenes The reaction of terminal alkenes with aryl iodides in the presence of 5 mol% of InCl 3 and sodium acetate produces stereoselectively internal E-aryl alkenes (40).…”

Section: Indium(iii) Chloridementioning

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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“…Indium(III) chloride catalyzes the microwave-assisted reaction of α-azidochalcones 34 with 1,3-dicarbonyl compounds 35 in water to form polysubstituted pyrroles 36 (Scheme 11) [42]. The reaction has been explained through the formation of an azirine intermediate.…”

Section: Formation Of Pyrrole Pyrrolidine and Pyrrolidinone Ringsmentioning

confidence: 99%