Literature DB >> 33575693

Synthesis of multi-substituted pyridines from ylidenemalononitriles and their emission properties.

Juliana M de Souza1, Irini Abdiaj2, Jiaqi Chen3, Kenneth Hanson3, Kleber T de Oliveira4, D Tyler McQuade2.   

Abstract

Numerous methodologies to obtain pyridines from ylidenemalononitriles are described in the literature. Nevertheless, they are limited to the use of microwave or conventional heat and few lead to 2,3,4 or 2,3,4,5-substituted pyridines as multi-proposal molecular scaffolds or even universal pyridines. Herein, we present a mild and facile solvent-free methodology to obtain a scope of multi-substituted pyridines at room temperature. We also report an example where one of the resulting amino-nicotinonitriles exhibits a preliminary evidence of aggregation-induced emission (AIE).

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Year:  2021        PMID: 33575693      PMCID: PMC7986046          DOI: 10.1039/d0ob02591g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  14 in total

1.  An efficient and chemoselective synthesis of N-substituted 2-aminopyridines via a microwave-assisted multicomponent reaction.

Authors:  Shujiang Tu; Bo Jiang; Yan Zhang; Runhong Jia; Junyong Zhang; Changsheng Yao; Feng Shi
Journal:  Org Biomol Chem       Date:  2006-12-04       Impact factor: 3.876

2.  Ylidenemalononitrile enamine-coated media as fluorescent "turn-on" probes for volatile primary amines.

Authors:  Ashley R Longstreet; Rebecca R Chandler; Tanmay Banerjee; L Zane Miller; Kenneth Hanson; D Tyler McQuade
Journal:  Photochem Photobiol Sci       Date:  2017-04-12       Impact factor: 3.982

3.  Restriction of Access to the Dark State: A New Mechanistic Model for Heteroatom-Containing AIE Systems.

Authors:  Yujie Tu; Junkai Liu; Haoke Zhang; Qian Peng; Jacky W Y Lam; Ben Zhong Tang
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336

4.  Real-time fluorescence quenching-based detection of nitro-containing explosive vapours: what are the key processes?

Authors:  P E Shaw; P L Burn
Journal:  Phys Chem Chem Phys       Date:  2017-11-15       Impact factor: 3.676

5.  Synthesis of aminonicotinonitriles and diaminopyridines through base-catalyzed ring transformation of 2H-pyran-2-ones.

Authors:  Farhanullah Farhanullah; Nidhi Agarwal; Atul Goel; Vishnu Ji Ram
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

6.  Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles.

Authors:  Ashley R Longstreet; Brian S Campbell; B Frank Gupton; D Tyler McQuade
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

7.  Diversity synthesis of N-substituted 2-amino-1,6-naphthyridine derivatives under microwave irradiation.

Authors:  Zheng-Guo Han; Chun-Bao Miao; Feng Shi; Ning Ma; Ge Zhang; Shu-Jiang Tu
Journal:  J Comb Chem       Date:  2010 Jan-Feb

8.  Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles.

Authors:  Juliana M de Souza; Irini Abdiaj; Jiaqi Chen; Kenneth Hanson; Kleber T de Oliveira; D Tyler McQuade
Journal:  J Org Chem       Date:  2020-08-28       Impact factor: 4.354

9.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

10.  Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine.

Authors:  Ashley R Longstreet; Suzanne M Opalka; Brian S Campbell; B Frank Gupton; D Tyler McQuade
Journal:  Beilstein J Org Chem       Date:  2013-11-20       Impact factor: 2.883

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