MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

Abstract

In the past decades, Multi-component reactions (MCRs) have been shown to be powerful tools for the synthesis of biologically active compounds and drug candidates from simple and readily accessible starting materials. 1 They offer significant advantages over conventional synthetic strategies by shortening reaction time, reducing waste, saving energy and making full use of starting materials. [2][3][4] Furthermore, the design of MCRs for the development of efficient chemical syntheses of complex and high added value molecules is another attractive area in chemistry. [5][6][7] Naphthoquinone derivatives particularly 3-substituted-2-hydroxy-1,4-naphthoquinones are of much importance because this fragment is a key moiety in numerous biologically active compounds. 8 For example as showed in the figure 1, atovaquone, lapachol, parvaquone and buparvaquone (Figure 1, first row) exhibit antimalarial, antibacterial, antiprotozoal, antitumor activities. 9 Similarly, pyrazolone framework is a well-known heterocycle in many drug substances of medicinal fields. To list some pyrazolone derivatives ( figure 1, seond row) such as antipyrine (phenazone), 4-aminopyrine (aminophenazone), metamizol (novalgin), and 4-isopropylpyrine (propyphenazone) are all useful antipyretic and analgesic drugs. 10 Pyrazolone derivatives also have ubiquitous applications in the development of acaricides, dyes, fungicides, herbicides, insecticides, inhibitors and reagents. [11][12][13][14][15][16][17] It is promising that the integration of these two bioactive units into a single molecule may exhibit new or improved pharmacological properties.Considering the above points, and also in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs. [18][19][20][21][22][23][24][25] Herein we wish to report MgCl 2 as a low-toxic catalyst for one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione

Synthesis of substituted pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines in the one-pot condensation of 2-thio-6-aminouracil, arylglyoxals and CH-acids

“…Одержання нових гетероциклічних сполук на основі простих і економічно обґрунтованих методик синтезу з доступних вихідних речовин постійно привертають увагу дослідників завдяки можливому використанню таких сполук в медицині [1][2][3]. Останнім часом велику популярність серед хіміків-органіків набули однореакторні мультикомпонентні реакції, які мають значні переваги у порівнянні з традиційними синтезами в плані виділення та очищення цільових сполук, використання "зелених розчинників", характеризуються більш високими виходами, хемо-та стерео-селективністю [4][5][6][7][8][9][10].…”

“…(J, Гц): 2.52 (3Н, с, SСН 3 ); 2.70 (3Н, с, СН 3 , DMF ); 2.86 (3Н, с, СН 3 , DMF); 3.13 (6Н, с, 2NСН 3 ); 5.14 (1Н, с, СН); 7.52 (2Н, д, J =8.4, Н, Ar); 7.59 (2Н, д, J =8. 4 4-оксо-4,7-дигідро-1H-пироло[2,3-d]піримідин-5-іл)-1,3диметилпіримідин-2,4,6(1H,3H,5H) 5-іл-1,3-диметилпіримідин-2,4,6(1H,3H,5H) 5-іл-1,3-диметилпіримідин-2,4,6(1H,3H,5H)…”

V2O5‐Catalyzed One‐Pot Multicomponent of Pyrazol Naphthoquinone as Scaffolds for Potential Bioactive Compounds: Synthesis, Structural Study and Cytotoxic Activity

“…Recent literature survey indicates that biologically active compounds were prepared by MCR reactions and most preferred catalysts employed for these reactions include MgCl 2 , P‐TSA, Bi(OTf) 3 , sulphamic acid and solvent free conditions . As per the concept of sustainable process design, catalyst should be available more abundant, cost effective and recyclable to an industrial standard.…”

One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

“…One‐pot, multicomponent reactions have many advantages such as simple isolation and purification steps, using green solvents, and more productivity with chemoselectivities and regioselectivities .…”