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Keywords = terminal ynones

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15 pages, 3443 KiB  
Article
Synthesis of Pyridin-1(2H)-ylacrylates and the Effects of Different Functional Groups on Their Fluorescence
by Weiguang Yang, Danyang Luo, Guanrong Li, Qiaoli Luo, Martin G. Banwell and Lanmei Chen
Molecules 2023, 28(18), 6511; https://doi.org/10.3390/molecules28186511 - 8 Sep 2023
Cited by 1 | Viewed by 1569
Abstract
While fluorescent organic materials have many potential as well as proven applications and so have attracted significant attention, pyridine–olefin conjugates remain a less studied subset of such systems. Herein, therefore, we report on the development of the straightforward syntheses of pyridin-1(2H)-ylacrylates [...] Read more.
While fluorescent organic materials have many potential as well as proven applications and so have attracted significant attention, pyridine–olefin conjugates remain a less studied subset of such systems. Herein, therefore, we report on the development of the straightforward syntheses of pyridin-1(2H)-ylacrylates and the outcomes of a study of the effects of substituents on their fluorescent properties. Such compounds were prepared using a simple, metal-free and three-component coupling reaction involving 2-aminopyridines, sulfonyl azides and propiolates. The fluorescent properties of the ensuing products are significantly affected by the positions of substituents on the cyclic framework, with those located in central positions having the greatest impact. Electron-withdrawing groups tend to induce blue shifts while electron-donating ones cause red shifts. This work highlights the capacity that the micro-modification of fluorescent materials provides for fine-tuning their properties such that they may be usefully applied to, for example, the study of luminescent materials. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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11 pages, 1941 KiB  
Article
Copper Catalyzed Inverse Electron Demand [4+2] Cycloaddition for the Synthesis of Oxazines
by Weiguang Yang, Zitong Zhou, Yu Zhao, Danyang Luo, Xiai Luo, Hui Luo, Liao Cui and Li Li
Catalysts 2022, 12(5), 526; https://doi.org/10.3390/catal12050526 - 7 May 2022
Cited by 3 | Viewed by 2701
Abstract
A copper catalyzed tandem CuAAC/ring cleavage/[4+2] annulation reaction of terminal ynones, sulfonyl azides, and imines has been developed to synthesize the functionalized oxazines under mild conditions. Particularly, the intermediate N-sulfonyl acylketenimines undergo cycloaddition of an inverse electron demand Diels–Alder reaction with imines [...] Read more.
A copper catalyzed tandem CuAAC/ring cleavage/[4+2] annulation reaction of terminal ynones, sulfonyl azides, and imines has been developed to synthesize the functionalized oxazines under mild conditions. Particularly, the intermediate N-sulfonyl acylketenimines undergo cycloaddition of an inverse electron demand Diels–Alder reaction with imines and a series of 1,3-oxazine derivatives were obtained successfully in good yields. Full article
(This article belongs to the Special Issue Catalysis in Green Chemistry and Organic Synthesis)
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