A fast and efficient 'on-solvent' cascade assembling of salicylaldehydes and dimethylbarbituric acid into 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones

被引：0

作者：

Elinson, Michail N. ^{[1
]}

Vereshchagin, Anatoly N. ^{[1
]}

Korshunov, Alexander D. ^{[1
]}

Egorov, Mikhail P. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

来源：

HETEROCYCLIC COMMUNICATIONS | 2018年 / 24卷 / 02期

关键词：

barbiturates; cascade reaction; catalysis; chromeno[2,3-d]pyrimidines; cyclization; salicylaldehydes; MALONONITRILE; SCAFFOLD; DERIVATIVES; WATER; COMBINATORIAL; ANTIPLATELET; CYCLIZATION; INHIBITORS; PROTOCOL; ISATINS;

D O I：

10.1515/hc-2018-0015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fast (15 min) and efficient cascade reaction of salicylaldehydes and 1,3-dimethylbarbituric acid in the presence of p-TsOH as a catalyst furnishes substituted 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H, 3H, 5H)-triones 1a-h, containing both chromeno[2,3-d]pyrimidine and hexahydropyrimidine-2,4,6-trione pharmacologically active fragments, in 95-99% yields. This new procedure is characterized by the use of inexpensive reagents and a simple workup.

引用

页码：79 / 83

页数：5

共 50 条

[31] Reaction of 5-(Arylmethylidene)-2,4,6-pyrimidine2,4,6(1H,3H,5H)-triones with Morpholine N-Oxide
A. G. Tyrkov
Russian Journal of Organic Chemistry, 2020, 56 : 939 - 941
[32] Effect of 5-(Arylmethylidene)-2,4,6-Pyrimidine-2,4,6(1H,3H,5H)-Triones on the Course of Experimental Leprosy Infection
M. Yu. Yushin
A. K. Ayupova
A. G. Tyrkov
F. K. Il’yasov
Pharmaceutical Chemistry Journal, 2022, 55 : 1019 - 1022
[33] Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones:: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings
Rezende, MC
Dominguez, M
Wardell, JL
Skakle, JMS
Low, JN
Glidewell, C
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O306 - O311
[34] Effect of 5-(Arylmethylidene)-2,4,6-Pyrimidine-2,4,6(1H,3H,5H)-Triones on the Course of Experimental Leprosy Infection
Yushin, M. Yu
Ayupova, A. K.
Tyrkov, A. G.
Il'yasov, F. K.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2022, 55 (10) : 1019 - 1022
[35] Crystal structure of 5-[bis(methylsulfonyl)methyl]-1,3-dimethyl-5-(methylsulfonyl)pyrimidine-2,4,6(1H, 3H, 5H)-trione
Mallah, Eyad
Al-Sheikh, Ahmed
Sweidan, Kamal
Abu Dayyih, Wael
Steimann, Manfred
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O58 - +
[36] Synthesis, Crystal Structure and DFT Studies of 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione
Sharma, Anamika
Jad, Yahya E.
Ghabbour, Hazem A.
de la Torre, Beatriz G.
Kruger, Hendrik G.
Albericio, Fernando
El-Faham, Ayman
CRYSTALS, 2017, 7 (01)
[37] Synthesis and in vitro Antibacterial Activities of 5-(2,3,4,5-Tetrahydro-1H-chromeno[2,3-d]pyrimidin-5-yl)pyrimidione Derivatives
Cheng Qingfang
Wang Qifa
Tan Ting
Wang Mingxiao
Chen Na
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (02) : 386 - 390
[38] 1,1′,3,3′,5,5′-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-pentaone
Pesyan, Nader Noroozi
Rastgar, Saeed
Hosseini, Yaser
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1444 - U3327
[39] Crystal Structure of 5,5′-(Furan-2-ylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione)
Sharma, Naresh
CRYSTALLOGRAPHY REPORTS, 2020, 65 (06) : 875 - 878
[40] Diastereoselective and Efficient Synthesis of Indeno[2",1":4′,5′]furo[3′,2′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione and 6-(2,3-Dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione Derivatives
Saberi, Dariush
Mohammadizadeh, Mohammad Reza
Esmaeili, Reza
HELVETICA CHIMICA ACTA, 2015, 98 (10) : 1411 - 1418

← 1 2 3 4 5 →