Reductive heterocyclizations via indium–iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles

Ahn, Gil Hwan; Lee, Jung June; Jun, Young Moo; Lee, Byung Min; Kim, Byeong Hyo

doi:10.1039/b707240f

Cited by 17 publications

(1 citation statement)

References 37 publications

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“…A variety of other methods including benzyne [3 + 2] cycloaddition, zincate addition to diazonium salts, and alkylation of 1 H -indazoles have also been reported . Among them, reductive cyclization of 2-nitrobenzylamines by using Sn, Ti, Zn and In have attracted considerable attention because of the readily available starting material . Nevertheless, these methods still suffer from setbacks such as unsatisfying yields, longer and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Dhole

Selvaraju

et al. 2018

ACS Comb. Sci.

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A novel and efficient method for the one-pot synthesis of 2 H-indazole from readily available building blocks is reported. The reaction of 2-nitrobenzylamines with zinc and ammonium formate underwent partial reduction to nitroso-benzylamine followed by an intramolecular cyclization to afford 2 H-indazole via N-N bond formation. The carboxylic acid moiety of indazole was proceeded to regioselective alkyne insertion under ruthenium catalysis to form pyranone-fused indazoles. The regioselectivity is influenced by the weak coordination of indazole ring nitrogen to the metal center.

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Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Dhole

Selvaraju

et al. 2018

ACS Comb. Sci.

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Reductive Heterocyclizations via Indium—Iodine‐Promoted Conversion of 2‐Nitroaryl Imines or 2‐Nitroarenes to 2,3‐Diaryl‐substituted Indazoles.

et al. 2007

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Pyrazole derivatives R 0180Reductive Heterocyclizations via Indium-Iodine-Promoted Conversion of 2-Nitroaryl Imines or 2-Nitroarenes to 2,3-Diaryl-substituted Indazoles. -Optimized conditions are found for the selective formation of the title indazoles from N-(2-nitrobenzylidene)anilines (imines) and anilines. In the presence of indium and iodine, an excess of the aniline undergoes the reductive cyclization with the imines in aprotic THF. Anilines with either the same or a different structure than that of the anilino subunit of the imine can be used. In the latter case, the resulting indazoles such as (VII) contain no "mixed" substituents. A one-pot preparation starting from the corresponding 2-nitrobenzaldehydes is also successfully performed. -(AHN, G. H.; LEE, J. J.; JUN, Y. M.; LEE, B. M.; KIM*, B. H.; Org.

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Indium Trichloride (InCl₃) Catalyzed Synthesis of Fused 7‐Azaindole Derivatives Using Domino Knoevenagel‐Michael Reaction

Dongare

Chavan

Surwase

et al. 2016

J Chinese Chemical Soc

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An efficient and high yielding methodology developed for the synthesis of fused 7‐azaindole derivatives via one pot multicomponent assembly process of cyclic 1,3‐dicarbonyls with substituted aldehydes and 5‐amino‐1‐tert‐butyl‐1H‐pyrrole‐3‐carbonitrile. The transformation occurs via domino Knoevenagel‐ Michael reaction followed by intramolecular cyclization in the presence of catalytic amount of InCl3 (10 mol %). Mild reaction conditions, easy isolation of products, and good to excellent yields in a shorter period of time are the silent features of present methodology. Structures of all the newly prepared compounds have been corroborated by various spectroscopic methods.

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Reductive heterocyclizations via indium–iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles

Cited by 17 publications

References 37 publications

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Reductive Heterocyclizations via Indium—Iodine‐Promoted Conversion of 2‐Nitroaryl Imines or 2‐Nitroarenes to 2,3‐Diaryl‐substituted Indazoles.

Indium Trichloride (InCl₃) Catalyzed Synthesis of Fused 7‐Azaindole Derivatives Using Domino Knoevenagel‐Michael Reaction

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Reductive heterocyclizations via indium–iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles

Cited by 17 publications

References 37 publications

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Reductive Heterocyclizations via Indium—Iodine‐Promoted Conversion of 2‐Nitroaryl Imines or 2‐Nitroarenes to 2,3‐Diaryl‐substituted Indazoles.

Indium Trichloride (InCl3) Catalyzed Synthesis of Fused 7‐Azaindole Derivatives Using Domino Knoevenagel‐Michael Reaction

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Indium Trichloride (InCl₃) Catalyzed Synthesis of Fused 7‐Azaindole Derivatives Using Domino Knoevenagel‐Michael Reaction