1532-84-9Relevant articles and documents
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Bergstrom,Rodda
, p. 3030 (1940)
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Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols
Baykov, Sergey V.,Boyarskaya, Irina A.,Boyarskiy, Vadim P.,Geyl, Kirill K.,Kasatkina, Svetlana O.
, p. 6059 - 6065 (2021/07/21)
A novel catalyst-free synthesis ofN-pyridin-2-yl,N-quinolin-2-yl, andN-isoquinolin-1-yl carbamates utilizes easily accessibleN-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of a wide range ofN-pyridin-2-yl orN-quinolin-2-yl substituted carbamates featuring electron-donating and electron-withdrawing groups in the azine rings and containing various primary, secondary, and even tertiary alkyl substituents at the oxygen atom (48-94%; 31 examples). The DFT calculation and experimental study showed that the reaction proceeds through the intermediate formation of hetaryl isocyanates. The method can be applied to obtainN-isoquinolin-1-yl carbamates, although in lower yields, and ethyl benzo[h]quinolin-2-yl carbamate has also been successfully synthesized (68%).
Heteroarylation method of amine
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Paragraph 0060-0070; 0076, (2021/02/24)
The invention discloses a heteroarylation method of amine, and the method comprises the following steps of: mixing an amine compound, heteroaromatic hydrocarbon, a photocatalyst and an organic solventto obtain a solution A; and in an inert gas atmosphere, irradiating the solution A with visible light, and carrying out reaction to obtain a heteroarylated product of amine. According to the method,under mild conditions, free radical coupling of amine compounds and heteroaromatic compounds is efficiently achieved through visible light irradiation, and various heteroarylamines are synthesized. The method has good functional group compatibility and high regioselectivity, can be further applied to later modification of bioactive molecules, and shows a good industrial application prospect.
Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis
Zhou, Chao,Lei, Tao,Wei, Xiang-Zhu,Ye, Chen,Liu, Zan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 16805 - 16813 (2020/11/09)
Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.
