Synthesis of arylated and aminated naphthalenes and their synthetic applications for aza-heterocycles

Singh, Surjeet; Shaw, Ranjay; Shally,; Chaudhary, Sandeep; Kumar, Abhinav; Pratap, Ramendra

doi:10.1016/j.tet.2016.08.044

Cited by 8 publications

(4 citation statements)

References 38 publications

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“…Based on deuterium incorporation studies, a plausible mechanism, involving initial attack of nitronate anion on nitrile followed by intramolecular recursive nitronate addition to triple bond and protonation, was proposed. Similar benzannulation reactions of 2‐(1‐cyano‐2,2‐bis(methylthio)vinyl)benzonitrile with nitromethane was also reported by Singh et al [54b] …”

Section: Domino Synthesis Of Bi‐ and Tricyclic Ringssupporting

confidence: 82%

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes as a source of recursive carbanions has created a niche operating space for generating molecular complexity and diversity. This new corollary i. e. recursive nitronate cyclization is the basis of a domino [5 C+1 C] cyclization strategy wherein nitroalkanes act as one‐carbon lynchpin, providing rapid access to topologically intriguing, densely functionalized carbo‐ and heterocycles embodying multiple chiral centers with regio‐, stereo‐ and enantioselectivity. Extension to aromatic domains, particularly via benzannulation reactions, has further consolidated the operating space. While leveraging the functional versatility of nitro group for post‐domino modifications, such endeavors have culminated in total synthesis of diverse natural products. An incisive analysis of recursive nitronate cyclizations and their emergent potentials is delineated in this review. It is hoped that this focused narrative will enthuse and draw new practitioners to the arena to advance the field.

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Section: Domino Synthesis Of Bi‐ and Tricyclic Ringssupporting

confidence: 82%

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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“…Sereda and coworkers have prepared aniline derivatives via a multi‐component reaction of ketone, aldehyde and two equivalent malononitrile in the presence of silica nano‐particles as a reusable catalyst in ethanol under reflux conditions [22] . In 2016, our group reported the synthesis of 4‐amino‐3‐ methyl/aryl‐2‐(methylthio)‐1‐naphthonitriles by the reaction of 2‐(1‐cyano‐2,2‐bis(methylthio)vinyl)benzonitrile with nitromethane and 1‐methyl‐2‐substituted‐4‐nitrobenzene at room temperature and 90 °C, respectively under basic conditions [23] . in 2014, our group has employed 2 H ‐pyran‐2‐ones and 2‐cyanomethyl benzonitrile for the synthesis of 2‐aminobenzo[ h ]quinolines via ring transformation strategy using NaNH 2 as a base in DMF at 100 °C [24] .…”

Section: Introductionmentioning

confidence: 99%

“…[22] In 2016, our group reported the synthesis of 4-amino-3-methyl/aryl-2-(methylthio)-1-naphthonitriles by the reaction of 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile with nitromethane and 1-methyl-2substituted-4-nitrobenzene at room temperature and 90 °C, respectively under basic conditions. [23] in 2014, our group has employed 2H-pyran-2-ones and 2-cyanomethyl benzonitrile for the synthesis of 2-aminobenzo[h]quinolines via ring transformation strategy using NaNH 2 as a base in DMF at 100 °C. [24] Later, our group published two articles exploring 2H-pyran-2ones and benzyl cyanide as starting materials, where reaction condition-dependent regioselectivity was observed for their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Multifunctional Arylated Anilines and Amino‐dihydrophenanthrenes Through Arylacetonitriles Mediated Ring Transformation of 2H‐Pyran‐2‐ones/2‐oxo‐benzo[h]chromenes

et al. 2023

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We are reporting a simple and efficient synthesis of highly functionalized aniline by the reaction of 2H-pyran-2-ones and benzyl cyanide in presence of sodamide in dioxane under reflux conditions. Various 4-sec.amino-2H-pyran-2-ones, 4methylsulfanyl-2H-pyran-2-ones and 2-oxobenzo[h[chromones were used as a substrate. Further, synthetic application of obtained arylated aniline was carried out to afford multifunc-tional carbazoles (13). 2''-Bromo-[1,1' : 2',1''-teraryl]-3'-amines ( 6) and 4-(2-bromoarylyl)-9,10-dihydrophenanthren-3-amines (11) was used to demonstrate the the synthesis of carbazoles. The structure of isolated product 11 d was ascertained by spectroscopic and single crystal X-ray diffraction analyses. We have explained the role of nonpolar solvents in the synthesis of arylated aniline.

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“…16 Recently, Dash et al devised a threestep procedure for synthesizing symmetrical and unsymmetrical 1,2-teraryls from various benzil derivatives, the Template for SYNTHESIS Thieme crucial step being ring closure metathesis using Grubb's second generation catalyst followed by dehydration (Scheme 1d). 17 In addition to the above-mentioned classical approaches, regioselective synthesis of 1,2-teraryls can also be accomplished by the carbanion induced ring transformation of 2H-pyran-2ones with various carbon nucleophiles such as substituted phenylacetones 18 and benzyl cyanide 19 (Scheme 1e).…”

mentioning

confidence: 99%

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Krishnan

Singh

2022

Synthesis

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The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound assisted carbanion induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls in high yields. This metal-free methodology provides easy access to a series of 1,2-teraryls and features broad functional group tolerance and mild reaction condition. Single crystal X-ray diffraction analysis of 4-(piperidin-1-yl)-6-(thiophen-2-yl)-[1,1'-biphenyl]-3-carbonitrile indicated that the crystal belongs to monoclinic system with a P21 space group having twisted aryl rings.

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Synthesis of arylated and aminated naphthalenes and their synthetic applications for aza-heterocycles

Cited by 8 publications

References 38 publications

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

Synthesis of Multifunctional Arylated Anilines and Amino‐dihydrophenanthrenes Through Arylacetonitriles Mediated Ring Transformation of 2H‐Pyran‐2‐ones/2‐oxo‐benzo[h]chromenes

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

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