Literature DB >> 23079670

Tandem inverse-electron-demand hetero-/retro-Diels-Alder reactions for aromatic nitrogen heterocycle synthesis.

Radleigh A A Foster1, Michael C Willis.   

Abstract

The merged inverse-electron-demand hetero-Diels-Alder (ihDA)/retro-Diels-Alder (rDA) reaction sequence can be used to rapidly synthesise highly functionalised nitrogen heteroaromatics. The reaction offers many advantages: high atom economy, high levels of regioselectivity, it rarely requires a catalyst and, in some cases, can be performed in the absence of solvent. In this tutorial review we discuss the range of commonly used dienophiles and aza-dienes for this process whilst highlighting the reactivity trends, and illustrating their applications.

Entities:  

Year:  2012        PMID： 23079670     DOI： 10.1039/c2cs35316d

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  12 in total

1.  Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids.

Authors:  Nicholas H Angello; Robert E Wiley; Tristan G Elmore; Ryan S Perry; Jonathan R Scheerer
Journal:  Org Lett       Date:  2018-08-10       Impact factor: 6.005

2.  Construction of hybrid polycyclic quinolinobenzo[a]phenazinone architectures using solid-state melt reaction (SSMR).

Authors:  Manickam Bakthadoss; Varathan Vinayagam
Journal:  Mol Divers       Date:  2020-05-04       Impact factor: 2.943

3.  Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels-Alder reactions.

Authors:  Salah Fadel; Youssef Hajbi; Mostafa Khouili; Said Lazar; Franck Suzenet; Gérald Guillaumet
Journal:  Beilstein J Org Chem       Date:  2014-01-28       Impact factor: 2.883

4.  Development of a mild and versatile directed cycloaddition approach to pyridines.

Authors:  Sylvestre P J T Bachollet; Jérôme F Vivat; Dean C Cocker; Harry Adams; Joseph P A Harrity
Journal:  Chemistry       Date:  2014-08-21       Impact factor: 5.236

5.  Strain-promoted reaction of 1,2,4-triazines with bicyclononynes.

Authors:  Katherine A Horner; Nathalie M Valette; Michael E Webb
Journal:  Chemistry       Date:  2015-08-13       Impact factor: 5.236

6.  Efficient DNA-Polymer Coupling in Organic Solvents: A Survey of Amide Coupling, Thiol-Ene and Tetrazine-Norbornene Chemistries Applied to Conjugation of Poly(N-Isopropylacrylamide).

Authors:  Thomas R Wilks; Rachel K O'Reilly
Journal:  Sci Rep       Date:  2016-12-16       Impact factor: 4.379

7.  The effect of Bu Zhong Yi Qi decoction on simulated weightlessness‑induced muscle atrophy and its mechanisms.

Authors:  Mu Zhu; Zhongyang Liu; Mingze Gao; Yan Zhang; Yuheng Li; Shukuan Ling; Pengfei Zhang; Chenyang Zhao; Lijun Jiang; Yu Liu; Qi Li; Dong Li; Sumin Hu; Yingxian Li
Journal:  Mol Med Rep       Date:  2017-08-18       Impact factor: 2.952

8.  Oxidation, Coordination, and Nickel-Mediated Deconstruction of a Highly Electron-Rich Diboron Analogue of 1,3,5-Hexatriene.

Authors:  Alexander Hermann; Felipe Fantuzzi; Merle Arrowsmith; Theresa Zorn; Ivo Krummenacher; Benedikt Ritschel; Krzysztof Radacki; Bernd Engels; Holger Braunschweig
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-01       Impact factor: 15.336

9.  Non-precious metals catalyze formal [4 + 2] cycloaddition reactions of 1,2-diazines and siloxyalkynes under ambient conditions.

Authors:  Chintan S Sumaria; Yunus E Türkmen; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005

Review 10.  Preparation and Utility of N-Alkynyl Azoles in Synthesis.

Authors:  Brandon Reinus; Sean M Kerwin
Journal:  Molecules       Date:  2019-01-24       Impact factor: 4.411
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