Literature DB >> 27063921

Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs).

Tanpreet Kaur1, Preeti Wadhwa1, Sourav Bagchi1, Anuj Sharma1.   

Abstract

The advent of cycloaddition reactions in the synthesis of heterocycles and their ever burgeoning applications in the fields of material chemistry, catalysis and drugs have been a profound scientific development. In particular, isocyanide based cycloaddition reactions have been harbingers of an exciting new chapter in the realms of organic synthesis. The emergence of numerous synthetic protocols utilizing formal cycloaddition of isocyanides with conjugated heterodienes has unleashed countless opportunities to design and synthesize diverse heterocyclic scaffolds. To date, there has not been any exclusive review on a formal [4+1] cycloaddition involving isocyanides. The present review highlights the journey of formal [4+1] cycloaddition reactions of isocyanides with diverse electrophilic substrates viz. oxadienes, azadienes, thioacyl imines, alkylidene amides, alkylidene hydrazines, α,β-unsaturated nitro compounds, α-thioxothioamides, nitroso alkenes, acyl imines, vinyl ketenes, vinyl isocyanates, etc. to afford functionalized pyrroles, imidazoles, furans, oxazoles, pyrazoles, etc.

Entities:  

Year:  2016        PMID: 27063921     DOI: 10.1039/c6cc01562j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  8 in total

1.  Addition of Isocyanide-Containing Amino Acids to the Genetic Code for Protein Labeling and Activation.

Authors:  Yuda Chen; Kuan-Lin Wu; Juan Tang; Axel Loredo; Jordan Clements; Jingqi Pei; Zane Peng; Ruchi Gupta; Xinlei Fang; Han Xiao
Journal:  ACS Chem Biol       Date:  2019-11-14       Impact factor: 5.100

2.  Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams.

Authors:  Zhanhao Liang; You-Chen Lin; Joshua G Pierce
Journal:  Org Lett       Date:  2021-11-30       Impact factor: 6.072

3.  New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized.

Authors:  Maryna V Murlykina; Maryna N Kornet; Sergey M Desenko; Svetlana V Shishkina; Oleg V Shishkin; Aleksander A Brazhko; Vladimir I Musatov; Erik V Van der Eycken; Valentin A Chebanov
Journal:  Beilstein J Org Chem       Date:  2017-05-31       Impact factor: 2.883

4.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

5.  Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke-Blackburn-Bienaymé Reaction/SNAr/Ring-Chain Azido-Tautomerization Strategy.

Authors:  Miguel Ángel Claudio-Catalán; Shrikant G Pharande; Andrea Quezada-Soto; Kranthi G Kishore; Angel Rentería-Gómez; Felipe Padilla-Vaca; Rocío Gámez-Montaño
Journal:  ACS Omega       Date:  2018-05-14

Review 6.  Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis.

Authors:  Jorge Heredia-Moya; Daniel A Zurita; José Eduardo Cadena-Cruz; Christian D Alcívar-León
Journal:  Molecules       Date:  2022-10-09       Impact factor: 4.927

7.  A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions.

Authors:  Shabnam Shaabani; Ahmad Shaabani; Monika Kucerakova; Michal Dusek
Journal:  Front Chem       Date:  2019-09-18       Impact factor: 5.221

Review 8.  Bioorthogonal Ligations and Cleavages in Chemical Biology.

Authors:  Youshan Li; Hua Fu
Journal:  ChemistryOpen       Date:  2020-08-14       Impact factor: 2.911

  8 in total

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