Nishimura, Yoshio; Kikuchi, Hidetomo; Kubo, Takanori; Gokurakuji, Yuki; Nakamura, Yuri; Arai, Rie; Yuan, Bo; Sunaga, Katsuyoshi; Cho, Hidetsura published an article in Tetrahedron Letters. The title of the article was 《Synthesis of 6-unsubstituted 2-oxo, 2-thioxo, and 2-amino-3,4-dihydropyrimidines and their antiproliferative effect on HL-60 cells》.Electric Literature of C7H13NO2 The author mentioned the following in the article:
A general and efficient synthetic method for 6-unsubstituted 3,4-dihydropyrimidin-2(1H)-thiones and -ones I (R = H, C6H5, 4-ClC6H4, etc., X = S, O) has been developed. In three-component reactions, the reactivity of reagents serving as the C5-C6 fragment of the dihydropyrimidine ring was compared. The reaction of thiourea or urea, aldehydes RCHO, and Et 3-(dimethylamino)acrylate in the presence of a catalytic amount of AlCl3 by smooth heating proceeds to give I in high yields. Synthetic novelty of the protocol are as follows: (1) Lewis acid-mediated reaction, (2) good to high yields, and (3) broad scope as for aldehydes and ureas. Hitherto unavailable 6-unsubstituted 2-aminodihydropyridimidines II (R = n-Pr, Ph) have been obtained from the 2-thioxo derivative I (X = S) by a stepwise method involving substitution reaction with the amine at the 2-position. The 6-unsubstituted compounds I and 6-Me derivatives III (R = cyclohexyl, n-Pr) were assessed for their antiproliferative effect on the human promyelocytic leukemia cell line, HL-60. The 4-propyl-6-Me derivative III (R = n-Pr) showed relatively strong activity with the IC50 value of 952 nM. The experimental part of the paper was very detailed, including the reaction process of Ethyl 3-(dimethylamino)acrylate(cas: 924-99-2Electric Literature of C7H13NO2)
Ethyl 3-(dimethylamino)acrylate(cas: 924-99-2) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Electric Literature of C7H13NO2
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