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Synthetic method of dialkyl amino dithiocarbamate alkyl ester
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A technology of alkyl dialkylaminodithiocarbamate and sodium phenethylaminodithiocarbamate, applied in organic chemical methods, sulfide preparation, organic chemistry, etc., can solve problems that have not been reported in the literature
Active Publication Date: 2020-01-14
CHENGDU UNIVERSITY OF TECHNOLOGY
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[0018] (o-methylbenzyl)trimethylammonium trifluoromethanesulfonate instead of benzyltrimethylammonium trifluoromethanesulfonate in Example 1 to obtain yellow oily liquid N,N-diethylaminodithioformic acid The yield of (2-methylbenzyl)ester was 95%.
[0023] (m-methylbenzyl)trimethylammonium trifluoromethanesulfonate instead of benzyltrimethylammonium trifluoromethanesulfonate in Example 1 to obtain yellow oily liquid N,N-diethylaminodithioformic acid The yield of (3-methylbenzyl)ester was 92%.
[0024] 1 H NMR (400MHz, CDCl 3 )δ7.24–7.06(m,3H),7.05–6.90(m,1H),4.42(s,2H),3.97(q,J=7.0Hz,2H),3.65(q,J=7.2Hz,2H ),2.26(s,3H),1.20(q,J=5.9, 5.2Hz,6H).
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Abstract
In organic sulfur compounds, dialkyl amino dithiocarbamatealkyl ester plays a very important role. Researches show that dialkyl amino dithiocarbamatealkyl ester and the derivatives thereof have widebiological characteristics and pharmacological activity. For example, many studies show that the dialkyl amino dithiocarbamatealkyl ester has various activities, including anti-proliferative, anti-glaucoma, antibacterial, antifungal, breast cancer treatment and cholinesterase inhibition activities, and can be used as a myocardial imaging agent. It is known that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof can be taken as inhibitors of HIV-1 NCp7, antiviral agents, and non-flavonoid TRPV1 antagonists. Dialkyl amino dithiocarbamate alkyl ester has a wide application range, and is massively produced in the world. The invention provides a method for efficiently synthesizing dialkyl amino dithiocarbamate alkyl ester. Under the catalysis of CuI, a chiral quaternaryammonium salt and a dialkyl amino dithioformate are used for C-S cross coupling for the first time, and dialkyl amino dithiocarbamate alkyl ester is prepared. The target product is further converted andcoupled with brominated aromatic hydrocarbons to obtain high-purity enantiomer chiral thioethers. The synthesis process has the advantages of mild reaction conditions, wide universality, no toxicity or danger, high yield, wide substrate range and the like.
Description
technical field [0001] This patent relates to the research fields of organic synthesis, drug synthesis, and organic chemical industry. The specific method is to synthesize dialkylaminodisulfide in one step through C-S cross-coupling of alkyl quaternaryammonium salt and dialkylaminodithioformate Alkylformate compounds. Background technique [0002] Dialkylcarbamate and its derivatives have a wide range of biological properties and pharmacological activities. Benzylcarbamate (such as 4-methoxybenzyl-N, N-diethylcarbamate) that exhibits excellent herbicidal activity against grasses and broad-leaved plants belongs to Dialkylaminodithiocarboxylates (S.Wakamori, Y.Yoshida, Y.Ishii, Agric.Biol.Chem.1969, 33, 1367–1376.) In addition, many studies have shown that dialkylamino Dithioformates also exhibit various biomedical activities, including antiproliferative (S.L.Cao, Y.Han, C.Z.Yuan, Y.Wang, Z.Xiahou, J.Liao, R.T.Gao, B.B.Mao, B.L.Zhao , Z.F.Li, X.Xu, Eur.J.Med.Chem.2013,64,...
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