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金刚烷胺类含胺化合物对 4,6-二氯嘧啶、2,6-二氯吡嗪和 1,3-二氯异喹啉的单胺化和二胺化反应。

Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines.

机构信息

Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, 119991 Moscow, Russia.

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, 119071 Moscow, Russia.

出版信息

Molecules. 2021 Mar 29;26(7):1910. doi: 10.3390/molecules26071910.

Abstract

-heteroaryl substituted adamantane-containing amines are of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of -heterocycles has been substituted by the amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of the second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine, and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

摘要

具有杂芳基取代的金刚烷胺类化合物因其具有潜在的抗病毒和心理治疗活性而备受关注。通过与一系列金刚烷基伯胺的亲核取代反应,在杂环的α-位氯原子被氨基取代。使用 NMR 光谱研究了这些化合物中的质子平衡。使用 Pd(0)催化,在 4-氨基-6-氯嘧啶、2-氨基-氯吡嗪和 1-氨基-3-氯异喹啉中引入了第二个氨基取代基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7550/8037717/ea38cec92e6c/molecules-26-01910-sch001.jpg

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