Application of Isocyanides as Amide Surrogates in the Synthesis of Diverse Isoindolin‐1‐one Derivatives by a Palladium‐Catalyzed Tandem Carboxamidation/Hydroamidation Reaction

Pathare, Ramdas S.; Sharma, Shivani; Sathish, Elagandhula; Saini, Vaishali; Sawant, Devesh; Yadav, Monika; Sharon, Ashoke; Khan, Shahnawaz; Pardasani, R. T.

doi:10.1002/ejoc.201600999

Cited by 27 publications

(13 citation statements)

References 77 publications

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“…If the temperature is raised to 160 °C, the generated bisamide undergoes a cyclocondensation to quinolinones 66 , which is accompanied by spontaneous de- tert -butylation. It should be noted that similar one-pot hydroxyimidoylation/cyclization cascades are also reported in the syntheses of indolin-1-ones [ 45 ] and fused dihydropyrrolimines [ 46 ].…”

Section: Pd 0 -Catalyzed Isocyanide Insertionsmentioning

confidence: 70%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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Section: Pd 0 -Catalyzed Isocyanide Insertionsmentioning

confidence: 70%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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“…In this context, Sawant, Khan, Pardasani, and co-workers developed a regio-and stereoselective method for the synthesis of 3-methyleneisoindolin-1-ones 116 by utilizing 1-aryl-2-(2-haloaryl)acetylenes 115 and tertiary isocyanides (Scheme 38). 94 This tandem reaction is greatly influenced by the electronic nature of the aryl substituents (Ar) at the distal end of the C≡C bond. Accordingly, electron-releasing aryl groups and/or alternating alkyl substituents rather than Ar sluggish the reaction at the carboxamidation stage.…”

Section: Scheme 37 Pd-catalyzed C-s Activation/isocyanide Insertion/hmentioning

confidence: 99%

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

et al. 2020

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The synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic molecules and pharmaceutical candidates. This review gives an overview of the achievements in isocyanide-based transition metal and inner transition metal catalyzed amide formation and discusses highlights of the proposed distinct mechanisms.1 Introduction2 Synthesis of Arenecarboxamides3 Synthesis of Alkanamides4 Synthesis of Cyclic Amides5 Formation of Alkynamides6 Formation of Acrylamide-like Molecules7 Formation of Ureas and Carbamates8 Conclusion

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“…A new C-C, C-O and C-N bond formation affording the final compounds in 65-92 % yields (Scheme 67). 97 The overall mechanism resulted to be equivalent (even considered as alternative) to the employment of a carbon monoxide insertion/generation of acyl-palladium species/ nucleophile addition amine as terminating step.…”

Section: Scheme 66 Synthesis Of Three Families Of Quinolines From 2cmentioning

confidence: 99%

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

2019

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The chemistry of palladium complexes has no limits. Many domino processes (even multicomponent) are continuously appearing in the literature. Carbocyclic and heterocyclic molecules are efficiently prepared under the atom economy principle using the smallest amount of the catalyst. The importance of the applications in many scientific areas of all these cyclic skeletons made this general methodology much more attractive.

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Application of Isocyanides as Amide Surrogates in the Synthesis of Diverse Isoindolin‐1‐one Derivatives by a Palladium‐Catalyzed Tandem Carboxamidation/Hydroamidation Reaction

Cited by 27 publications

References 77 publications

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

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