Recent Advances in the Synthesis of 5‐Membered<i>N</i>‐Heterocycles via Rhodium Catalysed Cascade Reactions

Mishra, Deepak R.; Panda, Bhabani Shankar; Nayak, Smita; Panda, Jasmine; Mohapatra, Seetaram

doi:10.1002/slct.202200531

Cited by 10 publications

(10 citation statements)

References 974 publications

(1,219 reference statements)

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“…The structure of the synthesized compound 6 e were characterized 1 H & 13 C NMR, HRMS and FTIR spectral analysis (Supporting information). 1…”

Section: Chemistryselectmentioning

confidence: 99%

“…The structure of the synthesized compound 5 c were characterized by 1 H & 13 C NMR, HRMS and FTIR spectral analysis (Supporting information). 1 H NMR of compound 5 c displayed two doublet of doublets in the region δ 7.37 ppm (dd, J 1 = 8.0 Hz, J 2 = 1.6 Hz, 1H), 6.91 (dd, J 1 = 8.0 Hz, J 2 = 1.2 Hz, 1H) and a triplet in the region 7.02 (t, J = 8.0 Hz, 1H) attributed to the aromatic CÀ H protons of chromene ring (i.e C7-H to C9-H) respectively. The chemical shift of C4-H proton of chromene ring and À OCH 3 both appeared as a singlet at δ 5.56 ppm (s, 2H) and δ 3.92 ppm (s, 3H) respectively.…”

Section: Characterisationmentioning

confidence: 99%

“…Both synthetic and medicinal applications of five-membered Nheterocycles are well explored in plethora of literature. [1] Among these, 1,2,3-triazoles are useful building blocks, having a wide range of industrial applications such as photosensitizers, dyes, agrochemicals and commercially employed as anticorrosive agents. [2][3][4] In past few years, the pharmacological applications of 1,2,3-triazole derivatives has gained progressive attention, owing to its stability toward light, moisture, oxygen, and metabolism in the body.…”

Section: Introductionmentioning

confidence: 99%

“…Polynitrogen based five‐membered heterocycles despite being obscure in nature, play an essential role in biological systems. Both synthetic and medicinal applications of five‐membered N ‐heterocycles are well explored in plethora of literature [1] . Among these, 1,2,3‐triazoles are useful building blocks, having a wide range of industrial applications such as photosensitizers, dyes, agrochemicals and commercially employed as anti‐corrosive agents [2–4] .…”

Section: Introductionmentioning

confidence: 99%

“…[1,2,3]triazole 5 a proceeded completion in 45 minutes with a noticeably lower yield i. e. 65 % compared to that of microwave method (entry 15).With optimized reaction condition in hand, we further utilized different 2H-chromene-3-carbonitrile derivatives 3 a-i to evaluate the scope of this methodology (Scheme 3).Withunsubstituted 2H-chromene-3-carbonitrile 3 a the reaction produced the expected 2,4-dihydrochromeno[3,4d][1,2,3]triazole product 5 a in very good yield (i. e. 86 %) (entry 1). A comparable result was observed when benzene ring of 2H-chromene-3-carbonitrile was replaced by naphthalene moiety 5 b (entry 2).…”

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confidence: 99%

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Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃

et al. 2022

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Conjugated cyano cyclo‐olefins modified as highly regioselective dipolarophiles in 1,3‐dipolar cycloaddition with NaN3 to synthesize corresponding fused 1,2,3‐triazole and 1H‐tetrazole derivatives. The first example of catalytic 1,3‐dipolar cycloaddition of NaN3 with 2H‐chromene‐3‐carbonitriles and subsequent elimination/cyclization of cyano functionality is designated. In presence of catalytic amount of p‐TSA or AgNO3, 2H‐chromene‐3‐carbonitriles react with NaN3 discretely producing 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles or 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles respectively, in good to excellent yields (i. e. 51–88 % or 85–97 %) with high regioselectivity and wide substrate scope adequacy.

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“…The structure of the synthesized compound 6 e were characterized 1 H & 13 C NMR, HRMS and FTIR spectral analysis (Supporting information). 1…”

Section: Chemistryselectmentioning

confidence: 99%

Section: Characterisationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃

et al. 2022

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Construction of Nitrogen Spirocycles in a Tandem Co(III)‐catalyzed C−H Activation/Dipolar Cycloaddition Reaction

Brześkiewicz,

Loska

2023

Adv Synth Catal

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Complex spirocyclic isoindolines and pyrrolidines are formed in a tandem process involving Co(III)‐catalyzed dienylation of cyclic C‐aryl nitrones with 2,3‐butadien‐1‐ol carbonates, followed by intramolecular 1,3‐dipolar cycloaddition. The nitrone moiety serves both as a directing group for the C(aryl)−H activation and the dipole in the cycloaddition step. High regioselectivity of the fused vs. bridged product can be obtained by adjusting the reaction temperature. Reactions with substituted allenic substrates provide heterocycles with additional stereocenters usually with complete diastereoselectivity. The reaction products were readily transformed further into other complex nitrogen‐containing spirocyclic systems.

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A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

Pant,

Prakash,

Dhami

2024

ChemistrySelect

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Catalytic carbonylation has gained a lot of interest over the past 20 years. It produced various pharmaceuticals, agrochemicals, and intermediates that can made through this process. The carbonylation process is the most straightforward method to insert CO into any organic substrate using a simple carbonyl source, i. e., CO gas. Apart from gaseous CO, many techniques have devised for producing CO in situ using surrogates such as HCOOH, DMF, Formic acid, Phenyl Formate, Oxalic acid, and Chloroform. Several carbonylation methods, such as aminocarbonylation, alkoxycarbonylation, double carbonylation, and oxidative carbonylation, provide viable and appealing substitutes for conventional synthetic methods on a commercial or laboratory scale. Many recent studies focus on catalyst‐product separation, catalyst recoverability, and reusability in these reactions. Therefore, advancements in using different approaches, such as supported liquid phase catalysis and biphasic catalysis, to anchor homogeneous catalysts are becoming increasingly important. These carbonylation methods are easy to use, cost‐effective, and do not require ligands. They also produce excellent yields of the products necessary. Using phosphine ligands has drawbacks, including high work‐up costs, laborious work‐up techniques, and sensitivity to air and moisture. Several phosphine‐free carbonylation pathways offer affordable and straightforward ways to accomplish these changes without phosphine ligands. This review summarizes the synthetic application of homogeneous and immobilized catalysts in producing carboxylic acid derivatives and heterocycles that have medicinal properties.

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Recent Advances in the Synthesis of 5‐MemberedN‐Heterocycles via Rhodium Catalysed Cascade Reactions

Cited by 10 publications

References 974 publications

Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃

Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃

Construction of Nitrogen Spirocycles in a Tandem Co(III)‐catalyzed C−H Activation/Dipolar Cycloaddition Reaction

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

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Recent Advances in the Synthesis of 5‐MemberedN‐Heterocycles via Rhodium Catalysed Cascade Reactions

Cited by 10 publications

References 974 publications

Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN3

Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN3

Construction of Nitrogen Spirocycles in a Tandem Co(III)‐catalyzed C−H Activation/Dipolar Cycloaddition Reaction

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

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Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃

Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN₃