Impact Factor: 5.6     h-index: 27

Document Type : Original Article

Authors

Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

Abstract

2-Amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carbonitrile 2 was prepared by the reaction of N-methylisatoic anhydride 1 with malononitrile via the ring-opening/ring closure pathway. The treatment of this compound with concentrated sulfuric acid at 100 °C gave a mixture of 2-amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 3 and 2-amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 4. The NMR analysis showed that the ratio of compound 3 to 4 in the mixture was one to two (1:2). When the later reactionwas performed in the presence of NaOH in refluxing H2O:EtOH, the compounds 3 and 4 were not formed, but instead, ring cleavage occurred to give compound 2-(methylamino) benzoic acid 5 in high yield. Density functional theory (DFT) calculations at the M06-2X/6-311+G(d,p) level of theory was also used to compute the 1H NMR chemical shifts of the compounds 3 and 4. Good agreement between the DFT-calculated 1H NMR chemical shifts and corresponding experimental values confirmed the suitability of the optimized geometries for these compounds. Characteristics of the bonding interactions were explored using the atoms in molecules (AIM) analysis.

Graphical Abstract

A Probe into Hydrolysis of Nitrile Moiety in 2-Amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Keywords

Main Subjects

[1].   Salaheldin A.M., Oliveira-Campos A.M.F., Rodrigues L.M., Synth. Commun., 2009, 39:1186
[2].   Ebrahimi Z., Davoodnia A., Motavalizadehkakhky A., Mehrzadc J., Eurasian Chem. Commun., 2020, 2:170
[3].   Khashi M., Davoodnia A., Lingam, V.P.R., Res. Chem. Intermed., 2015, 41:5731
[4].   Sajjadifar S., Hamidi H., Pal K., J. Chem. Rev., 2019, 1:35
[5].   Chakraborty R.R., Ghosh P., Asian J. Green Chem., 2018, 2:330
[6].   Niu W., Draths K.M., Frost J.W., Biotechnol. Prog., 2002, 18:201
[7].   Snead D.R., Jamison T.F., Angew. Chem., Int. Ed., 2014, 54:983
[8].   Rappoport Z., Patai S., Eds., The Chemistry of the Cyano Group, Wiley: London, 1970
[9].   Bailey P.D., Mills T.J., Pettecrew R., Price R.A., Comprehensive Organic Functional Group Transformations II, A.R. Katritzky, R.J.K. Taylor, Eds., Elsevier: Oxford, U.K., 2005, 5:201
[10].    North M., Parkins A.W., Shariff A.N. Tetrahedron Lett., 2004, 45:7625
[11].    Leung C.W., Zheng W., Zhou Z., Lin Z., Lau C.P., Organometallics, 2008, 27:4957
[12].    Chemat F., Poux M., Berlan J., J. Chem. Soc., Perkin Trans. 2, 1996, 15:1781
[13].    Debabov V.G., Yanenko A.S., Rev. J. Chem., 2011, 1:385
[14].    PüsküllüM O., Tekiner B., Suzen S., Mini-Rev. Med. Chem., 2013, 13:365
[15].    Zemtsova M.N., Zimichev A.V., Trakhtenberg P.L., Klimochkin Y.N., Leonova M.V., Balakhnin S.M., Bormotov N.I., Serova O.A., Belanov E.F. Pharm. Chem. J., 2011, 45:267
[16].    Wen X., Wang S.-B., Liu D.C., Gong G.H., Quan Z.S. Med. Chem. Res.,2015, 24:2591
[17].    Singh S.K., Singh S., Int. J. Pharm. Sci. Rev. Res., 2014, 25:295
[18].    Pinz M.P., Reis A.S., de Oliveira R.L., Voss G.T., Vogt A.G., do Sacramento M., Roehrs J.A., Alves D., Luchese C., Wilhelm E.A., Regul. Toxicol. Pharmacol., 2017, 90:72
[19].    Valadbeigi E., Ghodsi S., Iran. J. Pharm. Res., 2017, 16:554
[20].    Gopaul K., Shintre S.A., Koorbanally N.A., Anti-Cancer Agents Med. Chem.,2015, 15:631
[21].    Khidre R.E., Abdel-Wahab B.F., Abdel-Rehem Badria F., Lett. Drug Des. Discovery, 2011, 8:640
[22].    Muruganantham N., Sivakumar R., Anbalagan N., Gunasekaran V., Leonard J.T., Biol. Pharm. Bull., 2004, 27:1683
[23].    Ashok D., Ganesh A., Lakshmi B.V., Ravi S., Russ. J. Gen. Chem., 2014, 84:1237
[24].    Bano B., Arshia, Khan K.M., Kanwal, Fatima B., Taha M., Ismail N.H., Wadood A., Ghufran M., Perveen S., Eur. J. Med. Chem., 2017, 139:849
[25].    Park J.H., Lee H.S., J. Appl. Biol. Chem., 2015, 58:5
[26].    Ge R., Zhao Q., Xie Z., Lu L., Guo Q., Li Z., Zhao L., Eur. J. Med. Chem., 2016, 122:465
[27].    Ghodsi R., Azizi E., Zarghi A., Iran. J. Pharm. Res., 2016, 15:169
[28].    Sang Z., Pan W., Wang K., Ma Q., Yu L., Liu W., Bioorg. Med. Chem., 2017, 25:3006
[29].    Zhong F., Geng G., Chen B., Pan T., Li Q., Zhang H., Bai C., Org. Biomol. Chem., 2015, 13:1792
[30].    Zhai X., Bao G., Wang L., Cheng M., Zhao M., Zhao S., Zhou H., Gong P., Bioorg. Med. Chem., 2016, 24:1331
[31].    Kuhrt D., Ejaz S.A., Afzal S., Khan S.U., Lecka J., Sévigny J., Ehlers P., Spannenberg A., Iqbal J., Langer P., Eur. J. Med. Chem., 2017, 138:816
[32].    Chen C., Hou X., Wang G., Pan W., Yang X., Zhang Y., Fang H. Eur. J. Med. Chem., 2017, 133:11
[33].    Turnpenny P., Padfield A., Barton P., Teague J., Rahme L.G., Pucci M.J., Zahler R., Rubio A., J. Pharm. Biomed. Anal., 2017, 139:44
[34].    Aboul-Enein M.N., El-Azzouny A.M.A.E.S., Ragab F.A.F., Hamissa M.F., Arch. Pharm., 2017, 350:1600377
[35].    Reynolds K.A., LoughlinW .A., Young D.J.,  Mini-Rev. Med. Chem.,2013, 13:730
[36].    Ahmadinejad N., Talebi Tari M., Chem. Methodol., 2019, 3:55
[37].    Nakhaei A., Davoodnia A., Morsali A., Russ. J. Phys. Chem. A, 2018, 92:271
[38].    Ramazani A., Sheikhi M., Yahyaei H., Chem. Methodol., 2017, 1:28
[39].    Ettehadi Z., Davoodnia A., Khashi M., Ali Beyramabadi S., J. Struct. Chem., 2018, 59:1596
[40].    Shahzad H., Ahmadi R., Najafpour J., Adhami F., Eurasian Chem. Commu., 2020, 2:162
[41].    Habibi-Khorassani S.M., Dehdab M., Darijani M., Eurasian Chem. Commu., 2019, 1:378
[42].    Makiabadi B., Zakarianezhad M., Chem. Methodol., 2020, 4:191
[44].    Eshghi H., Khojastehnezhad A., Moeinpour F., Bakavoli M. Can. J. Chem., 2015, 93:749
[45].    Khojastehnezhad A., Eshghi H., Moeinpour F., Bakavoli M., Izadyar M., Tajabadi J., Struct. Chem., 2016, 27:1041
[46].    Davoodnia A., Bakavoli M., Bashash M., Roshani M., Zhiani R., Turk. J. Chem.,2007, 31:599
[47].    Davoodnia A., Bakavoli M., Mohseni S., Tavakoli-Hoseini N., Monatsh. Chem., 2008, 139:963
[48].    Davoodnia A., Zhiani R., Tavakoli-Hoseini N., Monatsh. Chem., 2008, 139:1405
[49].    Davoodnia A., Rahimizadeh M., Atapour-Mashhad H., Tavakoli-Hoseini N., Heteroat. Chem., 2009, 20:346
[50].    Davoodnia A., Bakavoli M., Moloudi R., Tavakoli-Hoseini N., Khashi M., Monatsh. Chem., 2010, 141:867
[51].    Gholipour S., Davoodnia A., Nakhaei-Moghaddam M., Chem. Heterocycl. Compd., 2015, 51:808
[52].    Davoodnia A., Nakhaei A., Tavakoli-Hoseini N. Z., Naturforsch., 2016, 71:219
[53].    Vazirimehr S., Davoodnia A., Nakhaei-Moghaddam M., Tavakoli-Hoseini N., Heterocycl. Commun., 2017, 23:65
[54].    Dorostkar-Ahmadi N., Davoodnia A., Tavakoli-Hoseini N., Behmadi H., Indian J. Heterocycl. Chem., 2018, 28:543
[55].    Teymooria E., Davoodnia A., Khojastehnezhad A., Hosseininasab N., Iran. Chem. Commun., 2019, 7:271
[56].    Dorostkar-Ahmadi N., Davoodnia A., Tavakoli-Hoseini N., Behmadi H., Z., Naturforsch., 2019, 74:175
[57].    Zhao Y., Schultz N.E., Truhlar D.G., J. Chem. Theory Comput., 2006, 2:364
[58].    Frisch M., Trucks G., Schlegel H., Scuseria G., Robb M., Cheeseman J., Montgomery Jr J., Vreven T., Kudin K., Burant J. Gaussian 03, revision B. 05; Gaussian, Gaussian 03, revision B. 05; Inc., Pittsburgh, PA, 2003
[59].    Cheeseman J.R., Trucks G.W., Keith T.A., Frisch M.J. J. Chem. Phys., 1996, 104:5497
[60].    Lu T., Chen F., J. Comput. Chem., 2012, 33:580
[61].    Bader R.F., Chem. Rev., 1991, 91:893
[62].    Rozas I., Alkorta I., Elguero J., J. Am. Chem. Soc., 2000, 122:11154
[63].    Singh R., Kumar A., Tiwari R., Rawat P., Manohar R., Struct. Chem., 2013, 24:713
[64].    Keith T.A., AIMAll (Version 13.05. 06), TK Gristmill Software, Overland Park KS, USA, 2013
[65].    Dong G., Wang S., Miao Z., Yao J., Zhang Y., Guo Z., Zhang W., Sheng C., J. Med. Chem., 2012, 55:7593
[66].    Tezer N., Karakus N., J. Mol. Model., 2009, 15:223
[67].    Mathammal R., Sangeetha K., Sangeetha M., Mekala R., Gadheeja S. J. Mol. Struct., 2016, 1120:1
[68].    Alpaslan Y.B., Gökce H., Alpaslan G., Macit M., J. Mol. Struct., 2015, 1097:171
[69].    Kanaani A., Ajloo D., Grivani G., Ghavami A., Vakili M., J. Mol. Struct., 2016, 1112:87
[70].    Espinosa E., Souhassou M., Lachekar H., Lecomte C. Acta Crystallogr. Sect. B: Struct. Sci., 1999, 55:563