Cyclic acyl amidines as unexpected C4-donors for fully substituted pyridine ring formation in the base mediated reaction with malononitrile

作者: Volodymyr Tkachuk , Vladyslava Merkulova , Iryna Omelchenko , Axelle Arrault , Olga Hordiyenko

DOI: 10.1016/J.TETLET.2019.06.038

关键词:

摘要: Abstract A new one-step, pseudo four-component approach for the synthesis of fully substituted pyridines via ring-opening cyclic acyl amidine 3-amino-1H-isoindol-1-one and its aza-analogues during reaction with malononitrile in presence sodium methoxide, followed by pyridine ring closure is reported. This method allows one-step preparation previously unknown 2-(pyridin-4-yl)(hetero)aryl carboxamides good yields under mild conditions.

参考文章(46)
Jay Wrobel, Arlene Dietrich, Shiela A. Woolson, Jane Millen, Michael McCaleb, Maria C. Harrison, Thomas C. Hohman, Janet Sredy, Donald Sullivan, Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents. Journal of Medicinal Chemistry. ,vol. 35, pp. 4613- 4627 ,(1992) , 10.1021/JM00102A016
Xue-Song Chen, Yu-Lin Wu, Di-Hua Chen, Synthesis of a New Cerebroside Isolated from Typhonium giganteum Engl Chinese Journal of Chemistry. ,vol. 21, pp. 937- 943 ,(2010) , 10.1002/CJOC.20030210743
Tummala R. K. Reddy, Roger Mutter, William Heal, Kai Guo, Valerie J. Gillet, Steven Pratt, Beining Chen, Library design, synthesis, and screening : Pyridine dicarbonitriles as potential prion disease therapeutics Journal of Medicinal Chemistry. ,vol. 49, pp. 607- 615 ,(2006) , 10.1021/JM050610F
A. Yu. Alekseeva, D. L. Mikhailov, I. N. Bardasov, O. V. Ershov, O. E. Nasakin, A. N. Lyshchikov, Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers Russian Journal of Organic Chemistry. ,vol. 50, pp. 244- 250 ,(2014) , 10.1134/S1070428014020171
Alberto S. Alvarez-Insúa, M. Lora-Tamayo, José L. Soto, Synthesis of heterocyclic compounds. II. A simple one‐step synthesis of pyridines from aldehydes and malononitrile Journal of Heterocyclic Chemistry. ,vol. 7, pp. 1305- 1309 ,(1970) , 10.1002/JHET.5570070612
Joachim Kranz, Ein neuer Weg zu 3-substituierten Phthalimidinen Chemische Berichte. ,vol. 100, pp. 2261- 2273 ,(1967) , 10.1002/CBER.19671000722
Heike Brötz-Oesterhelt, Igor Knezevic, Stephan Bartel, Thomas Lampe, Ute Warnecke-Eberz, Karl Ziegelbauer, Dieter Häbich, Harald Labischinski, Specific and Potent Inhibition of NAD+-dependent DNA Ligase by Pyridochromanones Journal of Biological Chemistry. ,vol. 278, pp. 39435- 39442 ,(2003) , 10.1074/JBC.M306479200
Yozo Ohtsuka, Chemistry of diaminomaleonitrile. 4. Nitrile hydration of the Schiff bases Journal of Organic Chemistry. ,vol. 10, pp. 827- 830 ,(1979) , 10.1021/JO01319A036
J. R. Piper, G. S. McCaleb, J. A. Montgomery, R. L. Kisliuk, Y. Gaumont, F. M. Sirotnak, Syntheses and antifolate activity of 5-methyl-5-deaza analogues of aminopterin, methotrexate, folic acid, and N10-methylfolic acid. Journal of Medicinal Chemistry. ,vol. 29, pp. 1080- 1087 ,(1986) , 10.1021/JM00156A029