Regioselectivity in the Multicomponent Reaction of 5-aminopyrazoles, Cyclic 1,3-diketones and Dimethylformamide Dimethylacetal Under Controlled Microwave Heating

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2012 Mar 17

PMID 22423269

Citations 8

Authors

Kamal Usef Sadek

Ramadan Ahmed Mekheimer

Tahany Mahmoud Mohamed

Moustafa Sherief Moustafa

Mohamed Hilmy Elnagdi

Affiliations

Soon will be listed here.

Abstract

The multicomponent reaction of 5-aminopyrazole derivatives with cyclic 1,3-dicarbonyl compounds and dimethylformamide dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded regioselectively 8,9-dihydropyrazolo[1,5-a]quinazolin-6(7H)-ones 6 rather than the corresponding dihydropyrazolo[5,1-b]quinazolin-8(5H)-ones 4.

Citing Articles

Microwave-assisted efficient one-pot synthesis of -(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines.

Moustafa M, Ahmed Mekheimer R, Al-Mousawi S, Abd-Elmonem M, El-Zorba H, Hameed A Beilstein J Org Chem. 2020; 16:1706-1712.

PMID: 32733614 PMC: 7372238. DOI: 10.3762/bjoc.16.142.

5-Amino-pyrazoles: potent reagents in organic and medicinal synthesis.

Shaabani A, Nazeri M, Afshari R Mol Divers. 2018; 23(3):751-807.

PMID: 30552550 DOI: 10.1007/s11030-018-9902-8.

Design, Synthesis and Antitumor Evaluation of Novel Pyrazolopyrimidines and Pyrazoloquinazolines.

El-Naggar M, Hassan A, Awad H, Mady M Molecules. 2018; 23(6).

PMID: 29882908 PMC: 6100441. DOI: 10.3390/molecules23061249.

A Novel Synthesis of Highly Functionalized Pyridines by a One-Pot, Three-Component Tandem Reaction of Aldehydes, Malononitrile and N-Alkyl-2-cyanoacetamides under Microwave Irradiation.

Ahmed Mekheimer R, Al-Sheikh M, Medrasi H, Alsofyani N Molecules. 2018; 23(3).

PMID: 29522435 PMC: 6017934. DOI: 10.3390/molecules23030619.

A facile, regioselective synthesis of novel 3-(N-phenylcarboxamide)pyrazolo[1,5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their antibacterial activities.

Kaping S, Boiss I, Singha L, Helissey P, Vishwakarma J Mol Divers. 2015; 20(2):379-90.

PMID: 26511367 DOI: 10.1007/s11030-015-9639-6.

References

Chebanov V, Saraev V, Desenko S, Chernenko V, Knyazeva I, Groth U . Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes. J Org Chem. 2008; 73(13):5110-8. DOI: 10.1021/jo800825c. View

Kappe C . Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed Engl. 2004; 43(46):6250-84. DOI: 10.1002/anie.200400655. View

Erkkila A, Majander I, Pihko P . Iminium catalysis. Chem Rev. 2007; 107(12):5416-70. DOI: 10.1021/cr068388p. View

Chebanov V, Saraev V, Desenko S, Chernenko V, Shishkina S, Shishkin O . One-pot, multicomponent route to pyrazoloquinolizinones. Org Lett. 2007; 9(9):1691-4. DOI: 10.1021/ol070411l. View

McQuaid L, Smith E, South K, Mitch C, Schoepp D, True R . Synthesis and excitatory amino acid pharmacology of a series of heterocyclic-fused quinoxalinones and quinazolinones. J Med Chem. 1992; 35(18):3319-24. DOI: 10.1021/jm00096a002. View

Orvieto F, Branca D, Giomini C, Jones P, Koch U, Ontoria J . Identification of substituted pyrazolo[1,5-a]quinazolin-5(4H)-one as potent poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Bioorg Med Chem Lett. 2009; 19(15):4196-200. DOI: 10.1016/j.bmcl.2009.05.113. View

Kessler M, Baudry M, Lynch G . Quinoxaline derivatives are high-affinity antagonists of the NMDA receptor-associated glycine sites. Brain Res. 1989; 489(2):377-82. DOI: 10.1016/0006-8993(89)90875-5. View

Watson C, Whish W, Threadgill M . Synthesis of 3-substituted benzamides and 5-substituted isoquinolin-1(2H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP). Bioorg Med Chem. 1998; 6(6):721-34. DOI: 10.1016/s0968-0896(98)00029-7. View

Cravotto G, Cintas P . Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem Soc Rev. 2006; 35(2):180-96. DOI: 10.1039/b503848k. View

10.

Hoz A, Diaz-Ortiz A, Moreno A . Microwaves in organic synthesis. Thermal and non-thermal microwave effects. Chem Soc Rev. 2005; 34(2):164-78. DOI: 10.1039/b411438h. View

11.

Domling , Ugi I . Multicomponent Reactions with Isocyanides. Angew Chem Int Ed Engl. 2000; 39(18):3168-3210. DOI: 10.1002/1521-3773(20000915)39:18<3168::aid-anie3168>3.0.co;2-u. View