Ecofriendly and simple synthesis of pyrano[3,2-c]quinolone in water via an efficient one-pot three-component reaction European Journal of Chemistry 9 (1) (2018) 44-48 European Journal of Chemistry View Journal Online View Article Online Ecofriendly and simple synthesis of pyrano[3,2-c]quinolone in water via an efficient one-pot three-component reaction Ibrahim Ali Radini 1, Sameh Ramadan El-Gogary 1,2, Mohamed Sabri Mostafa 1,*, Bander Alnagei 1, Mohammed Mudarbish 1 and Shadad Dash 1 1 Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia iradini4@gmail.com (I.A.R.), selgogary@gmail.com (S.R.E.), ms-mostafa@hotmail.com (M.S.M.), bander-k-s-a@hotmail.com (B.A.), mudarbish@gmail.com (M.M.), shalidsh1993@gmail.com (S.D.) 2 Chemistry Department, Faculty of Science, Damietta University, New Damietta, 34518, Egypt * Corresponding author at: Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia. Tel: +966.050.8945386 Fax: +966.017.3230028 e-mail: ms-mostafa@hotmail.com (M.S. Mostafa). 10.5155/eurjchem.9.1.44-48.1679 Received: 28 December 2017 Received in revised form: 27 January 2018 Accepted: 28 January 2018 Published online: 31 March 2018 Printed: 31 March 2018 Pyrano[3,2-c]quinolones are commonly found in alkaloids, manifesting diverse biological activities. In this work, 2-amino-6-methyl-5-oxo-4-substituted-5,6-dihydro-4H-pyrano[3,2- c]quinoline-3-carbonitriles and ethyl 2-amino-4-(substituted)-6-methyl-5-oxo-5,6-dihydro- 4H-pyrano[3,2-c]quinoline-3-carboxylates have been synthesized efficiently from reaction of 4-hydroxy-1-methylquinolin-2(1H)-one, aldehydes and active methylene nitriles in one-pot three component reaction in aqueous medium, containing catalytic amount of ethanolamine resulting in 70-95% yields. Ethanolamine One pot reaction Pyranoquinolinone 4-Hydroxyquinolinone Multicomponent reaction Cinnamonitrile derivatives Cite this: Eur. J. Chem. 2018, 9(1), 44-48 Journal website: www.eurjchem.com 1. Introduction Synthesis of pyrano[3,2-c]quinolone, as the parent ring structure of pyranoquinoline alkaloids, has received signi- ficant attention in previous years due to the broad spectrum of their biological properties such as antimicrobial [1-3], anti- inflammatory [4], antimalarial [5]. Many of these alkaloids exhibit antiproliferative and anti-tubulin activities and are investigated as potential anticancer agents [6]. Examples for these cytotoxic alkaloids includes N-methylfindersine (1) and melicobisquinolinone B (2) which obtained via phytochemical studies on leaves of Melicope ptelefolia (Rutaceae) [7 ] as well as zanthosimuline (3), and huajiaosimuline (4) [8] (Figure 1). Nowadays, multicomponent reactions (MCR) strategy have attracted many attentions in organic and medicinal chemistry to produce biologically active compounds [9-11]. We herein report a safe, facile, fast and high yielding, eco-friendly synthesis of pyranoquinolones derivatives via an efficient one- pot three component reaction of 4-hydroxyquinolone with aldehydes and malononitrile or ethyl cyanoacetate in water. 2. Experimental 2.1. Instrumentations Melting points were obtained on a Gallenkamp melting point apparatus. 1H NMR spectra were performed on a Bruker (600 MHz) Ultra Shield Avance III spectrometer using TMS as an internal standard and CDCl3 as solvents. Chemical shifts were expressed as δ ppm. The IR spectra were performed on a Jasco 4100 FTIR spectrophotometer (KBr pellet). The electron impact (EI) mass spectra were performed on a Shimadzu GCMS-QP 1000 EX mass spectrometer at 70 eV. The Elemental analyses were performed on a Perkin Elmer’s 2400 Series II CHN elemental analyzer. 2.2. Synthesis 2.2.1. General procedure for the synthesis of pyrano[3,2-c] quinolones (8a-c and 11a,b) ABSTRACT RESEARCH ARTICLE KEYWORDS European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2018 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679 http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679 https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.1.44-48.1679&domain=pdf&date_stamp=2018-03-31 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679 mailto:iradini4@gmail.com mailto:selgogary@gmail.com mailto:ms-mostafa@hotmail.com mailto:bander-k-s-a@hotmail.com mailto:mudarbish@gmail.com mailto:shalidsh1993@gmail.com mailto:ms-mostafa@hotmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.1.44-48.1679&domain=pdf&date_stamp=2018-03-31� Radini et al. / European Journal of Chemistry 9 (1) (2018) 44-48 45 N O CH3 O N O CH3 O O N O CH3 O Me Me N O CH3 N CH3 O O 1 2 3 4 Figure 1. Examples of pyranoquinolone alkaloids exhibit cytotoxic activity. N O OH CH3 N O O CH3 NH2 CN CN NC R + a, R= H b, R= p-OMe c, R= m-Br CN CN CHO + N O OH CH3 + Water / Ethanolamine 5 5 8a-c6a-c 7 9a-c Procedure B Procedure A Water / Ethanolamine or Ethanol / piperidine R R Scheme 1 Procedure A: A cinnamonitrile derivatives (9a-c) (0.01 mol for each) were added to a solution of 4-hydroxy-1-methyl- quinolin-2(1H)-one (5) (0.01 mol) in 30 mL of distilled water which containing few drops of ethanolamine as a catalyst. The reaction mixture was stirred at room temperature for 20-180 minutes (Table 1). The solid product, which formed, was collected by filtration, washed by cold water and crystallized from ethanol. Procedure B: A mixture of 4-hydroxy-1-methylquinolin- 2(1H)-one (5), active methylene compound (malononitrile (7) and/or ethyl cyanoacetate (10)) and corresponding aromatic aldehyde (6a-d) in water and in presence of catalytic amount of ethanolamine (0.05 mmol) was stirring at room tempe- rature. The precipitate was collected by filtration and washed with water and recrystallized from ethanol (Scheme 1 and 2). 2-Amino-6-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3, 2-c]quinoline-3-carbonitrile (8a): Color: White. Yield: 80%. M.p.: 200-204 °C. FT-IR (KBr, ν, cm-1): 3328-3319 (NH2), 3107 (=CH), 2935 (-CH), 2198 (nitrile), 1677 (CO), 1604 (C=C). 1H NMR (600 MHz, CDCl3, δ, ppm): 3.86 (s, 3H, N-CH3), 4.36 (s, 1H, pyran H-4), 4.47 (s, 2H, NH2), 7.20-8.00 (m, 9H, ArH). MS (EI, m/z (%)): 329 (M+, 53.21), 314 (M+-CH3, 2.61), 252 (M+-C6H5, 100), 285 (M+-CH2NO, 29.17), 263 (M+-C3H2N2, 14.11), 247 (M+-C3H3N2O, 0.94), 201 (M+-C9H6N, 1.01), 157 (M+-C10H8N2O, 0.4), 118 (M+-C12H9N2O2, 1.81), 89 (M+-C13H12N3O2, 5.65). Anal. calcd. for C20H15N3O2: C, 72.94; H, 4.59; N, 12.76. Found: C, 72.92; H, 4.59; N, 12.75%. 2-Amino-4-(4-methoxyphenyl)-6-methyl-5-oxo-5,6-dihydro- 4H-pyrano[3,2-c]quinoline-3-carbonitrile (8b): Color: White. Yield: 85%. M.p.: 230-233 °C. FT-IR (KBr, ν, cm-1): 3370-3311 (NH2), 3154 (=CH), 2217 (nitrile), 1670 (CO), 1608 (C=C), 1238 (C-N). 1H NMR (600 MHz, CDCl3, δ, ppm): 2.93 (s, 3H, O- CH3), 3.91 (s, 3H, N-CH3), 4.72 (s, 1H, pyran H-4), 4.90 (s, 2H, NH2), (m, 8H, ArH). MS (EI, m/z (%)): 359 (M+, 36.78), 328 (M+-OMe, 5.08), 293 (M+-C3H2N2, 70.44), 292 (M+-C3H3N2, 99.65), 277 (M+-C3H2N2O, 5.31), 252 (M+-C7H7O, 40.88), 186 (M+-C10H9N2O, 8.01), 170.05 (M+-C10H9N2O2, 3.08), 157 (M+- C11H10N2O2, 4.47), 129 (M+-C12H10N2O3, 18.35), 133 (M+- C13H10N2O2, 12.83), 105.05 (M+-C14H10N2O3, 100), 89 (M+- C14H13N3O3, 19.25), 76 (M+-C15H13N3O3, 15.53). Anal. calcd. for C21H17N3O3: C, 70.18; H, 4.77; N, 11.69. Found: C, 70.17; H, 4.78; N, 11.70%. 2-Amino-4-(3-bromophenyl)-6-methyl-5-oxo-5,6-dihydro- 4H-pyrano[3,2-c]quinoline-3-carbonitrile (8c): Color: White. Yield: 70 %. M.p.: 255-257 °C. FT-IR (KBr, ν, cm-1): 3324-3297 (NH2), 3197 (=CH), 2981 (CH), 2198 (nitrile), 1670 (CO), 1619(C=C), 1254 (C-N). 1H NMR (600 MHz, CDCl3, δ, ppm): 3.65 (s, 3H, N-CH3), 4.74 (s, 1H, pyran H-4), 4.77 (s, 2H, NH2), 7.17-7.98 (m, 8H, ArH). MS (EI, m/z (%)): 407 (M+, 18.02), 408 (M+, 7.26), 409 (M+,19.77), 363 (M+-CH2NO, 6.81), 362 (M+- CH3NO, 3.71), 341.95 (M+ -C3H3N2, 6.3), 328.1 (M+-Br, 6.39), 252 (M+-C6H4Br, 100), 225 (M+-C7H8BrN, 2.21), 207 (M+- C7H7BrNO, 3.88), 157 (M+-C10H7BrN2O, 3.41), 129 (M+- C11H7BrN2O2, 2.77), 105 (M+-C13H7BrN2O2, 4.72), 76 (M+- C14 H10BrN3O2, 12.05). Anal. calcd. for C20H14 BrN3O2: C, 58.84; H, 3.46; N, 10.29. Found: C, 58.82; H, 3.46; N, 1028%. Ethyl 2-amino-4-(4-methoxyphenyl)-6-methyl-5-oxo-5,6-di hydro-4H-pyrano[3,2-c]quinoline-3-carboxylate (11a): Color: White. Yield: 78 %. M.p.: 225-227 °C. FT-IR (KBr, ν, cm-1): 3297-3216 (NH2), 3085 (=CH), 2985 (CH), 1681 (CO), 1623 (CO), 1604 (C=C), 1234 (C-N). 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.1.44-48.1679 46 Radini et al. / European Journal of Chemistry 9 (1) (2018) 44-48 Table 1. Yield percentage and reaction time for the synthesized compounds. Compound Procedure A Procedure B t (min) Yield (%) t (min) Yield (%) 8a 65 86 70 80 8b 75 80 90 85 8c 20 77 50 70 11a 120 65 180 78 11b 40 92 60 95 N O OH CH3 N O O CH3 NH2 CO2Et Water Ethanolamine CO2Et NC + 11a, R= OMe 11b, R= Cl CO2Et CN CHO + N O OH CH3 + Water / Ethanolamine or Ethanol / piperidine 5 5 6b,d 10 Procedure B Procedure A R R R 12a, R= OMe 12b, R= Cl Scheme 2 1H NMR (600 MHz, CDCl3, δ, ppm): 1.21 (t, 3H, J = 6.9 Hz, CH3), 3.63 (s, 3H, N-CH3), 3.76 (s, 3H, O-CH3), 4.14 (q, 2H, J = 6.9 Hz, CH2), 5.04 (s, 1H, pyran H-4 ), 6.35 (s, 2H, NH2), 6.65- 8.00 (m, 8H, ArH). MS (EI, m/z (%)): 406 (M+, 55.3), 361 (M+- C2H5O, 4.82), 360 (M+-C2H6O, 12.07), 333 (M+-C3H5O2, 30.43), 332 (M+-C3H6O2, 10.8), 299 (M+-C7H7O, 100), 293(M+-C5H7NO2, 8.13), 277 (M+-C5H7NO3, 1.42), 254 (M+-C9H12O2, 13.87), 253 (M+-C9H13O2, 82.8), 226 (M+-C10H12O3, 5.16), 170 (M+- C12H14NO4, 7.83), 157 (M+-C13H15NO4, 2.36), 142 (M+- C13H14NO5, 2.17), 105 (M+-C16H15NO4, 3.4), 104 (M+-C16H16NO5, 11.92), 76 (M+-C17H18N2O5, 3.52). Anal. calcd. for C23H22 N2O5: C, 67.97; H, 5.46; N, 6.89. Found: C, 67.98; H, 5.46; N, 6.90%. Ethyl 2-amino-4-(4-chlorophenyl)-6-methyl-5-oxo-5,6-dihyd ro-4H-pyrano[3,2-c]quinoline-3-carboxylate (11b): Color: White. Yield: 95%. M.p.: 222-225 °C. FT-IR (KBr, ν, cm-1): 3293-3215 (NH2), 3085 (=CH), 2985 (CH), 1685 (CO), 1654 (CO), 1619 (C=C),1226(C-N). 1H NMR (600 MHz, CDCl3, δ, ppm): 1.18 (t, 3H, J = 6.9 Hz, CH3), 3.64 (s, 3H, N-CH3), 4.13 (q, 2H, J = 6.9, CH2), 5.05 (s, 1H, pyran H-4), 6.40 (s, 2H, NH2), 7.16-8.00 (m, 8H, ArH). MS (EI, m/z (%)): 410 (M+, 30.77), 411 (M+, 7.73), 412 (M+, 9.98), 365 (M+-C2H5O, 4.3), 364 (M+-C2H6O, 3.55), 337 (M+-C3H5O2, 17.42), 299 (M+-C6H4Cl, 100), 281 (M+- C5H7NO3, 0.55), 226 (M+-C9H9ClO2, 2.58), 170 (M+-C11H11ClNO3, 4.11), 157 (M+-C12H12ClNO3, 0.25), 129 (M+-C13H12ClNO4, 1.44), 118 (M+-C14H13ClNO4, 1.13), 89 (M+-C15H16ClN2O4, 2.18), 76 (M+-C16H16ClN2O4, 2.9). Anal. calcd. for C22H19Cl N2O4: C, 64.32; H, 4.66; N, 6.82. Found: C, 64.33; H, 4.64; N, 6.83%. 3. Results and discussion It has been reported that the reaction of 4-hydroxy-2- quinolinone with α,β-unsaturated nitriles, as two component system, had afforded pyrano[3,2-c]quinolone derivatives. This reaction was carried out in refluxing ethanol for 50 minutes, using triethylamine as catalyst, and the pyranoquinolones were obtained in 64-95% yields [12,13]. Herein, we present the reobtaining pyrano[3,2-c]quinolone derivatives through modified facile, fast, higher yielding and ecofriendly proce- dure. In this procedure, we have used ethanolamine instead of triethylamine and replaced ethanol by water, the most clean, greenest and economic solvent (procedure A, Scheme 1). Thus, stirring of 4-hydroxy-1-methylquinolin-2(1H)-one (5) and α- cyano-cinnamonitriles (9a-c) in water containing catalytic amount of ethanolamine, at room temperature, afforded the expected solid products (8a-c) in 70-95% yields based on the isolated products, which were in considerable degrees of purity. On the other hand, pyrano[3,2-c]quinolone derivatives (8a-c) were also prepared by efficient technique of one-pot three component reaction (procedure B, Scheme 1). Thus, compound 5, the appropriate aldehyde 6a-c and malononitrile 7 were allowed to react together, under the suitable reaction conditions, to afford the same respective pyrano[3,2-c]quino- lone derivatives (8a-c). This confirmation reaction was carried out twice, once in water and once, else, in ethanol (procedure B, Scheme 1) as the reaction solvent and, always, the planned pyrano[3,2-c]quinolone derivatives were obtained. Thin layer chromatography (TLC), melting points and mixed melting points of pyrano[3,2-c]quinolone prepared by mixing of equal amounts of compound 8 obtained out of procedures A and B (Scheme 1), have been used to confirm obtaining the same respective derivative 8 through the different procedures. Also, structures of compound 8a-c are established for the reaction product based on the 1H NMR spectra which revealed the presence of a signal at δ 4.5-5.0 ppm for one proton linked with a sp3 carbon as 4H-pyran. Infrared spectrum of compound 8a, as an example, revealed absorption bands at 3319-3328 cm-1 for NH2 and at 2198 cm-1 for cyano group. On replacing the α-cyano-cinnamonitrile derivatives 9a-c by the, relatively lesser reactive α-carbo- ethoxycinnamonitriles (12a,b) in the above mentioned reactions A and B, Scheme 2, the corresponding pyrano[3,2- c]quinolone derivatives (11a,b) were obtained, but after a 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.1.44-48.1679 Radini et al. / European Journal of Chemistry 9 (1) (2018) 44-48 47 N O OH CH3 H2N-CH2CH2-OH N O O CH3 - N O O CH3 : NC R ArH N O O CH3 Ar NC R- + H+ N O O CH3 Ar C R N H N O OH CH3 Ar C R N : N O CH3 O NH Ar R N O CH3 O NH2 Ar R 5 8a-c a, R = CN Ar = Ph b, R = CN Ar = (p-OCH3)Ph c, R = CN Ar = (m-Br)Ph 9a-c and 12a,b 11a,b a, R = COOC2H5 Ar = (p-OCH3)Ph b, R = COOC2H5 Ar = (p-Cl)Ph 8a-c & 11a,b Scheme 3 much larger reaction time of 150-180 minutes and in a good yield of products of 78-90%. The same trend of results was, generally, obtained on carrying out the one-pot three-compo- nent reactions of compound 5, the appropriate aldehyde (6b,d) and ethyl cyanoacetate (10) (procedure B, Scheme 2) as an unambiguous synthesis, confirming the formation of the respective pyrano[3,2-c]quinolone derivatives. The postu- lated structure of compound 11a,b was based on the following arguments: a) mixed melting point ; b) TLC; c) 1H NMR spectra of compound 11b, as an example, showed signals at δ 1.18 (t, 3H, J = 6.9, CH3), 3.64 (s, 3H, N-CH3), 4.13 (q, 2H, J = 6.9, CH2), 5.05 (s, 1H, pyran H-4), 6.40 (s, 2H, NH2) and 7.16-8.00 ppm (m, 8H, ArH); d) FT-IR spectra of compound 11a-c exhibited absorption bands at 3297-3215 cm-1 for amino group, 1685 cm-1 for carbonyl ester group and at 1654 cm-1 for carbonyl of quinolone. Using two component condensation, the formation of compounds 8a-c and 11a,b were assumed to proceed via addition of quinolinyl C-3 to the activated double bond in α,β- unsaturated nitriles (9a-c) and (12a,b) followed by cyclo- addition of the Michael adduct (Scheme 3). Using three component condensations, the mechanism may occur by Knoevenagel condensation, Michael addition, intramolecular cyclization, and isomerization. α,β-Unsaturated nitriles is formed by Knoevenagel condensation of aldehyde (6a-d) and malononitrile (7) or ethyl cyanoacetate (10) by the action of ethanolamine. Then, the proton of 4-hydroxy-2(1H)-quinolone (5) is abstracted by ethanolamine to form carbanion which in Michael addition on compounds 9a-c and 12a,b leads to the formation of 2-amino-4H-pyrano[3,2-c]quinolin-5(6H)-one derivatives (8a-c) and (11a,b) through cyclization and isomerization. 4. Conclusion In this study 2-amino-6-methyl-5-oxo-4-substituted-5,6- dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles and ethyl 2-amino-4-(substituted)-6-methyl-5-oxo-5,6-dihydro-4H- pyrano[3,2-c]quinoline-3-carboxylates were prepared through modified facile, fast, high-yield and eco-friendly procedure. Acknowledgment The authors extend their appreciation to the Deanship of Scientific Research at Jazan University for funding this paper through the research group Project no. 019-FS3. Disclosure statement Conflict of interests: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. Funding Jazan University http://dx.doi.org/10.13039/100009388 ORCID Ibrahim Ali Radini https://orcid.org/0000-0003-2835-4874 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.1.44-48.1679 http://dx.doi.org/10.13039/100009388 https://orcid.org/0000-0003-2835-4874 48 Radini et al. / European Journal of Chemistry 9 (1) (2018) 44-48 Sameh Ramadan El-Gogary https://orcid.org/0000-0002-0465-4023 Mohamed Sabri Mostafa https://orcid.org/0000-0003-3537-3598 Bander Alnagei https://orcid.org/0000-0001-5513-7838 Mohammed Mudarbish https://orcid.org/0000-0002-5754-4995 Shadad Dash https://orcid.org/0000-0002-2602-0080 References [1]. Asghari, S.; Ramezani, S.; Mohseni, M. Chin. Chem. Lett. 2014, 25, 431- 434. [2]. Hassanin, H.; Ibrahim, M.; Alnamer, Y. Turk. J. Chem. 2012, 36, 682- 699. [3]. Fujita, Y.; Oguri, H.; Oikawa, H. J. Antibiot. 2005, 58, 425-427. [4]. Chen, J. J.; Chen, P. H.; Liao, C. H.; Huang, S. Y.; Chen, I. S. J. Nat. Prod. 2007, 70, 1444-1448. [5]. 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