Microwave-Assisted Preparation of Quinolone and Quinoline Derivatives

Abstract

Quinolinone derivatives can be obtained in microwave-assisted syntheses by reaction of aniline derivatives with acetylene dicarboxylic esters, a malonic acid diester or β-keto ester derivatives. The reaction proceeds under mild conditions in short reaction times. Two of the quinolinones were transformed into the corresponding 4-chloroquinolines either by conventional heating or in a microwave-assisted reaction. Further modifications resulted in the formation of the boron adduct or in an agglomerate. The latter was characterized by X-ray crystal structure analysis.

Key words

quinoline - quinolinone - one-pot synthesis - microwave

References and Notes

• 1a Michael JP. Nat. Prod. Rep.  2001,  18:  543 
• 1b Balasubramanian M. Kelay JG. In Comprehensive Heterocyclic Chemistry II   Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.245 
• 2 Polanski J. Zouhiri F. Jeanson L. Desmaele D. d’Angelo J. Mouscadet J.-F. Gieleciak R. Gasteiger J. Le Bret M. J. Med. Chem.  2002,  45:  4647 
• 3a Kacprzak K. Gawronski J. Synthesis  2001,  961 
• 3b Yoon TP. Jacobsen EN. Science  2003,  299:  1691 
• 4 Hollingshead RGW. Oxine and its Derivatives   Buttersworths; London: 1954. 
• 5 Albrecht M. Fiege M. Osetska O. Coord. Chem. Rev.  2008,  252:  812 
• 6 Albrecht M. . Schiffers S. Osetska O. Raabe G. Wieland T. Russo L. Rissanen K. Eur. J. Org. Chem.  2007,  2850 
• 7a Abass M. Heterocycles  2005,  65:  901 
• 7b Kouznetsov VK. Vargas Méndez LY. Meléndez Gómez CM. Curr. Org. Chem.  2005,  9:  141 
• 7c Larsen LD. Kai D. Quinolines, In Science of Synthesis   Georg Thieme Verlag; Stuttgart: 2005. 
• 7d Skraup K. Ber. Dtsch. Chem. Ges.  1880,  13:  2086 
• 7e Mansake RHF. Kulka M. Org. React.  1953,  7:  59 
• 7f Friedländer P. Ber. Dtsch. Chem. Ges.  1882,  15:  2572 
• 7g Gould RG. Jacobs WA. J. Am. Chem. Soc.  1939,  61:  2890 
• 8a Kappe CO. Stadler A. Microwaves in Organic and Medicinal Chemistry   Wiley-VCH; Weinheim: 2005. 
• 8b Hamelin J. Bazureau J.-P. Texier-Boulet F. In Microwaves in Organic Synthesis   Loupy A. Wiley-VCH; Weinheim: 2002.  p.253 
• 9a Kidwai M. Misra P. Kumar R. Saxena RK. Gupta R. Bradoo S. Monatsh. Chem.  1998,  129:  961 
• 9b Sabitha G. Babu RS. Reddy BVS. Yadav JS. Synth. Commun.  1999,  29:  4403 
• 9c Perzyna A. Houssin R. Barbry D. Hénichart J.-P. Synlett  2002,  2077 
• 9d Ranu BC. Hajra A. Jana U. Tetrahedron  2003,  59:  813 
• 9e Ranu BC. Hajra A. Jana U. Tetrahedron Lett.  2000,  41:  531 
• 9f Gãinã L. Cristea C. Moldovan C. Porumb D. Surducan E. Deleanu C. Mahamoud A. Barbe J. Silberg IA. Int. J. Mol. Sci.  2007,  8:  70 
• 9g Jia C.-S. Zhang Z. Tu S.-J. Wang G.-W. Org. Biomol. Chem.  2006,  4:  104 
• 9h Theoclitou M. Robinson LA. Tetrahedron Lett.  2002,  43:  3907 
• 9i Yadav JS. Reddy VS. Rao RS. Naveenkumar V. Nagaiah K. Synthesis  2003,  1610 
• 9j Chaudhuri MK. Hussain S. J. Chem. Sci.  2006,  118:  199 
• 9k Duvelleroy D. Perrio C. Parisel C. Lasne M.-C. Org. Biomol. Chem.  2005,  3:  3794 
• 9l Alexandre F.-R. Berecibar A. Wrigglesworth R. Besson T. Tetrahedron  2003,  59:  1413 
• 10a Schramm OG. Oeser T. Kaiser M. Brun R. Müller TJJ. Synlett  2008,  359 
• 10b For the synthesis of functionalized quinolines, see: Bernini R. Cacchi S. Fabrizi G. Filisti E. Sferrazza A. Synlett  2009,  1245 
• 12 Zewge D. Chen C. Deer C. Dormer PG. Hughes DL. J. Org. Chem.  2007,  72:  4276 
• 13 Lauer WM. Arnold RT. Tiffany B. Tinker J. J. Am. Chem. Soc.  1946,  68:  1268 
• 14 For 10, see: Wright R. Gordon M. Synthesis  1984,  1058 
• 15a For 16, see: Stephen JML. Tonkin IM. Walker J. J. Chem. Soc.  1947,  1034 
• 15b For 18, see: Etter MC. Urbanczyk-Lipkowska Z. Zia-Ebrahimi M. Panunto TW. J. Am. Chem. Soc.  1990,  112:  8415 
• 16 Agui H. Mitani T. Nakashita M. Nakagome T. J. Heterocycl. Chem.  1971,  8:  357 

11

Microwave experiments were performed using a CEM Discover BenchMate Plus microwave oven with IR temperature detection. Preparation of 4: O-Anisidine (0.123 g, 1.0 mmol), dimethyl acetylenedicarboxylate (0.156 g, 1.1 mmol) and Ph₂O (6 mL) were placed in a 10 mL vessel, which was sealed with a septum. The flask was placed in the MW cavity and was locked with the pressure device. MW irradiation at 120 ˚C without air-cooling was used during the first 5 min of reaction time, and then irradiation power was increased to 250 ˚C for the next 15 min. After cooling to r.t., the reaction mixture was diluted with n-hexane (150 mL).
A brown oil or solid precipitated. Solvent was removed and the residue was washed with n-hexane and recrystallized from acetone-n-hexane to yield a colourless crystalline solid in 54% yield. Characterization of key products: The analytical data of 4,^¹² 7 ^¹³ and 20 ^¹³ were in agreement with literature data. Derivative 19: Mp 146 ˚C. ^¹H NMR (400 MHz, CDCl₃): δ = 8.32 (s, 1 H), 7.84 (dd, J = 8.5, 1.1 Hz, 1 H), 7.68 (dd, J = 8.5, 8.0 Hz, 1 H), 7.15 (dd, J = 8.0, 1.1 Hz, 1 H), 4.10 (s, 3 H), 4.05 (s, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 165.0 (C), 156.1 (C), 146.1 (C), 143.7 (C), 140.1 (C), 130.1 (CH), 128.6 (C), 121.8 (CH), 115.4 (CH), 108.9 (CH), 56.3 (CH₃), 53.2 (CH₃). MS (EI, 70 eV): m/z (%) = 251.0(36) [M]⁺, 235.9 (100) [M - Me]⁺. IR (KBr): 3094, 1721, 1611, 1557, 1498, 1470, 1448, 1334, 1259, 1204, 1139, 1108, 1009, 969, 896, 819, 784, 747 cm^-¹. Anal. Calcd for C₁₂H₁₀ClNO₃˙1/3H₂O (257.7): C, 55.94; H, 4.17; N, 5.44. Found: C, 55.70; H, 4.10; N, 5.56.

17

CCDC 761359 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone], E-mail: [e-mail]].