Synthesis of naphtho- and pyrazolo-fused systems by an intramolecular Friedel–Crafts approach

Hassan A. K. Abd El-Aal

doi:10.1071/CH23030

RESEARCH ARTICLE

Previous Next Contents Vol 76(11)

Synthesis of naphtho- and pyrazolo-fused systems by an intramolecular Friedel–Crafts approach

Hassan A. K. Abd El-Aal

^A ^*

+ Author Affiliations

- Author Affiliations

^A Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt.

^* Correspondence to: hassankotb33@yahoo.com, hassankotb@aun.edu.eg

Handling Editor: Anastasios Polyzos

Australian Journal of Chemistry 76(11) 760-773 https://doi.org/10.1071/CH23030

Submitted: 11 February 2023 Accepted: 16 July 2023 Published online: 15 August 2023

Abstract

Efficient access to the tetracyclic pyrazolo-fused carbo- and N-heterocyclic systems: naphtho[2′,1′:3,4]cyclohepta[2,1-c]pyrazolones, naphtho[2′,1′:5,4]azepino[6,7-c]pyrazolones, naphtho[2′,1′:5,4]azocino[6,7-c]pyrazolones and naphtho[2′,1′:6,5]azonino[7,8-c]pyrazolones is described involving intramolecular Friedel–Crafts cycliacylations of synthesized pyrazole-based carboxylic acid or ester derivatives aided by treatment with Lewis and Brønsted acids. The required starting carbaldehyde was obtained by the Vilsmeier–Haack reaction of the corresponding 2-acetylnaphthalene hydrazone. Our developed strategy, involving a three-step route, offers easy access to tetracyclic pyrazole-fused systems in moderate to good yields.

Keywords: acylation mechanism, azepinopyrazolones, azocinopyrazolone, catalytic inhibition, cycloheptapyrazolones, Friedel–Crafts cycliacylations, trifluoromethanesulfonic acid.

References

1 Becerra D, Abonia R, Castillo J-C. Molecules 2022; 27: 4723-4805.
| Crossref |

2 Dias LRS, Salvador RRS. Pharmaceuticals 2012; 5: 317-324.
| Crossref |

3 Naim MJ, Alam O, Nawaz F, Alam MJ, Alam P. J Pharm Bioall Sci 2016; 8: 2-17.
| Crossref |

4 Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A, Rahisuddin A. Bioorg Chem 2016; 69: 77-90.
| Crossref |

5 Kees KL, Fitzgerald JJ, Steiner KE, Mattes JF, Mihan B, Tosi T, Mondoro D, McCaleb ML. J Med Chem 1996; 39: 3920-3928.
| Crossref |

6 Wiley RH. Chapter II. Pyrazolin‐5‐ones. 10. Sulfonic acids and derivatives, 3‐pyrazolin‐5‐ones. In: Wiley PF, editor. Pyrazolones, Pyrazolidones and Derivatives. New York, NY, USA: Wiley; 1964. Vol. 20, pp. 101–102.

7 Jamwal A, Javed A, Bhardwaj V. J Pharm BioSci 2013; 3: 114-125.

8 Häufel J, Breitmaier E. Angew Chem Int Ed Engl 1974; 13: 604.
| Crossref |

9 Li X, Yu Y, Tu Z. Molecules 2021; 26: 1202.
| Crossref |

10 Michon V, Hervé du Penhoat C, Tombret F, Gillardin JM, Lepage F, Berthon L. Eur J Med Chem 1995; 30: 147-155.
| Crossref |

11 Cottineau B, Toto P, Marot C, Pipaud A, Chenault J. Bioorg Med Chem Lett 2002; 12: 2105-2108.
| Crossref |

12 Sadeghpour M, Olyaei A. Res Chem Intermed 2021; 47: 4399-4441.
| Crossref |

13 Castillo J-C, Portilla J. Recent advances in the synthesis of new pyrazole derivatives. In: Attanasi OA, Merino P, Spinelli D, editors. Targets in Heterocyclic Systems: Chemistry and Properties. Rome, Italy: Società Chimica Italiana. 2018. Vol. 22, pp. 194–223.

14 Chebanov VA, Sakhno YI, Desenko SM, Chernenko VN, Musatov VI, Shishkina SV, Shishkin OV, Kappe CO. Tetrahedron 2007; 63: 1229-1242.
| Crossref |

15 Brullo C, Spisani S, Selvatici R, Bruno O. Eur J Med Chem 2012; 47: 573-579.
| Crossref |

16 Hu J, Chen S, Sun Y, Yang J, Rao Y. Org Lett 2012; 14: 5030-5033.
| Crossref |

17 Ebenezer O, Shapi M, Tuszynski JA. Biomedicines 2022; 10: 1124.
| Crossref |

18 Maddila S, Jonnalagadda SB, Gangu KK, Maddila SN. Curr Org Synth 2017; 14: 634-653.
| Crossref |

19 Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot YN, Al-Aizari FA, Ansar M. Molecules 2018; 23: 134-219.
| Crossref |

20 Mali G, Shaikh BA, Garg S, Kumar A, Bhattacharyya S, Erande RD, Chate AV. ACS Omega 2021; 6: 30734-30742.
| Crossref |

21 Kumar SV, Yadav SK, Raghava B, Saraiah B, Ila H, Rangappa KS, Hazra A. J Org Chem 2013; 78: 4960-4973.
| Crossref |

22 Baselt R. Disposition of Toxic Drugs and Chemicals in Man, 11th edn. Seal Beach, CA, USA: Biomedical Publications; 2017. pp. 894–895.

23 Ouyang G, Chen Z, Cai XJ, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY, Zeng S. Bioorg Med Chem 2008; 16: 9699-9707.
| Crossref |

24 Xu Y, Sun P, Song Q, Lai X, Liu W, Xia T, Huang Y, Shen Y. Eur J Org Chem 2017; 2017: 2998-3002.
| Crossref |

25 Saikia A, Barthakur MG, Borthakur M, Saikia CJ, Bora U, Boruah RC. Tetrahedron Letts 2006; 47: 43-46.
| Crossref |

26 Buckingham J, Baggaley KH, Roberts AD, Szabó LF. Dictionary of alkaloids, 2nd edn. Boca Raton, FL, USA: CRC Press; 2010.

27 Eicher T, Hauptmann S. The Chemistry of Heterocycles: Structure, Reactions, Synthesis and Applications. New York, NY, USA: Wiley-VCH; 2003.

28 Tewari AK, Singh VP, Yadav P, Gupta G, Singh A, Goel RK, Shinde P, Mohan CG. Bioorg Chem 2014; 56: 8-15.
| Crossref |

29 Santos NE, Carreira ARF, Silva VLM, Braga SS. Molecules 2020; 25: 1364.
| Crossref |

30 Kumar V, Kaur K, Gupta GK, Sharma AK. Eur J Med Chem 2013; 69: 735-753.
| Crossref |

31 Yet L. Five-membered rings with two heteroatoms, and their fused carbocyclic derivatives. In: Black D, Cossy J, Stevens C, editors. Comprehensive Heterocyclic Chemistry IV; 2022. pp. 1–112.

32 Misra AK, Sharma PK., Sedative and hypnoticdrugs. In: Uddin MS, Rashid M, editors. Advances in Neuropharmacology: Drugs and Therapeutics. New York, NY, USA: Apple Academic Press; 2020. p. 441.

33 Honour JW, Sudan HL, Lovell G. Biomed Chromatogr 1986; 1: 151-154.
| Crossref |

34 Castro J, Maddern J, Garcia-Caraballo S, Lumsden AL, Lindstrom B, Adams J, Brierley S. Gastroenterology 2019; 156: S-382.
| Crossref |

35 Elguero J. 3.01 – Pyrazoles. In: Katritzky AR, Rees CW, Scriven EFV, editors. Comprehensive Heterocyclic Chemistry II. Vol. 3. Five‐membered rings with two heteroatoms and fused carbocyclic derivatives. Oxford, UK: Pergamon Press; 1996. pp. 1–75.

36 Boolell M, Gepi-Attee S, Gingell JC, Allen MJ. J Br J Urol 1996; 78: 257-261.
| Crossref |

37 Pacher P, Nivorozhkin A, Szabó C. Pharmacol Rev 2006; 58: 87-114.
| Crossref |

38 Syed YY. Drugs 2019; 79: 93-98.
| Crossref |

39 Nichols DJ, Muirhead GJ, Harness JA. Br J Clin Pharmacol 2002; 53: 5S-12S.
| Crossref |

40 Schwartz BG, Kloner RA. Circulation 2010; 122: 88-95.
| Crossref |

41 Kloner RA. Am J Cardiol 2005; 96: 42-46.
| Crossref |

42 Castro J, Maddern J, Garcia-Caraballo S, Lumsden AL, Lindstrom B, Adams J, Brierley S. Gastroenterology 2019; 156(Suppl. 1): S382.

43 Tonani R, Bindi S, Fancelli D, Pittala V, D’Anello M. Heterobicyclic pyrazole derivatives as kinase inhibitors. US Patent 20060160874; New York, NY, USA: Scully Scott Murphy & Presser PC; 2006.

44 Mekheimer RA, Ahmed EA, Sadek KU. Tetrahedron 2012; 68: 1637-1667.
| Crossref |

45 Chen Z, Wu J. Org Lett 2010; 12: 4856-4859.
| Crossref |

46 Bhat BA, Puri SC, Qurishi MA, Dhar KL, Qazi GN. Synth Commun 2005; 35: 1135-1142.
| Crossref |

47 Borah B, Dwivedi KD, Chowhan LR. Arkivoc 2021; 2021: i, 273-328.
| Crossref |

48 Eman M, Kamel ST, Gaballah YMA, Nadia RM. Egypt J Chem 2010; 53: 731-744.
| Crossref |

49 Chauhan P, Mahajan S, Enders D. Chem Commun 2015; 51: 12890-12907.
| Crossref |

50 Deng X, Mani NS. Org Lett 2006; 8: 3505-3508.
| Crossref |

51 Donohue AC, Pallich S, McCarthy TD. J Chem Soc, Perkin Trans 1 2001; 2001(21): 2817-2822.
| Crossref |

52 Oh LM. Tetrahedron Lett 2006; 47: 7943-7946.
| Crossref |

53 Chiericato M, Dalla Croce P, Carganico G, Maiorana S. Heterocycl Chem 1979; 16: 383-384.
| Crossref |

54 Fustero S, Román R, Sanz-Cervera JF, Simón-Fuentes A, Cuñat AC, Villanova S, Murguía M. J Org Chem 2008; 73: 3523-3529.
| Crossref |

55 Mohamed Ahmed MS, Kobayashi K, Mori A. Org Lett 2005; 7: 4487-4489.
| Crossref |

56 Daidone G, Plescia S. J Heterocycl Chem 1982; 19: 689-690.
| Crossref |

57 Daidone G, Sprio V, Plescia S, Marino ML, Bombieri G, Bruno G. J Chem Soc, Perkin Trans 2 1989; 1989(2): 137-141.
| Crossref |

58 Maggio B, Raffa D, Raimondi MV, Cusimano MG, Plescia F, Cascioferro S, Cancemi G, Lauricella M, Carlisi D, Daidone G. Eur J Med Chem 2014; 72: 1-9.
| Crossref |

59 Sharma SC, Lynch BM. Can J Chem 1979; 57: 3034-3040.
| Crossref |

60 Aubert T, Farnier M, Meunier I, Guilard R. J Chem Soc Perkin Trans 1 1989; 13: 2095-2098.
| Crossref |

61 Miklós F, Kanizsai I, Sohár P, Stájer G. J Mol Struct 2002; 610: 41-46.
| Crossref |

62 Batchu H, Batra S. Tetrahedron Lett 2014; 55: 6236-6239.
| Crossref |

63 Heaney H. Addition–elimination reactions (acylations) – the bimolecular aromatic Friedel–Crafts reaction. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford, UK: Pergamon Press; 1991. Vol. 2, pp. 733–752.

64 Wales SM, Walker MM, Johnson JS. Org Lett 2013; 15: 2558-2561.
| Crossref |

65 Roberts RM, Khalaf AA. Friedel–Crafts Chemistry: A Century of Discovery. New York, NY, USA: Marcel Dekker; 1984.

66 Barclay LRC. Cyclialkylation of aromatics. In: Olah GA, editor. Friedel–Crafts and Related Reactions. Volume II. Alkylation and Related Reactions. Part II. Wiley Interscience; 1964. pp. 785–977.

67 Olah GA. Friedel–Crafts Chemistry. New York, NY, USA: Wiley; 1973.

68 Zhao Y-L, Lou Q-X, Wang L-S, Hu W-H, Zhao J-L. Angew Chem Int Ed 2017; 56: 338-342.
| Crossref |

69 Effenberger F, Epple G. Angew Chem Int Ed Engl 1972; 11: 299-300.
| Crossref |

70 Sethna S. General aspects. In: Olah GA, editor. Friedel–Crafts and Related Reactions. New York, NY, USA: Interscience; 1964. Vol. 3, pp. 911–1002.

71 Ross J, Xiao JL. Green Chem 2002; 4: 129-133.
| Crossref |

72 Anand RV, Baktharaman S, Singh VK. J Org Chem 2003; 68: 3356-3359.
| Crossref |

73 Johnson WS. Org React 1944; 2: 114-177.

74 Kubo A, Saito N, Yamato H, Masubuchi K, Nakamura M. J Org Chem 1988; 53: 4295-4310.
| Crossref |

75 Jørgensen KA. Synthesis 2003; 2003(7): 1117-1125.
| Crossref |

76 Yadav JS, Gayathri KU, Subba-Redy BV, Prasad AR. Synlett 2009; 2009: 43-46.
| Crossref |

77 Sharma R, Kumar R, Kumar R, Upadhyay P, Sahal D, Sharma U. J Org Chem 2018; 83: 12702-12710.
| Crossref |

78 Tireli M, Maračić S, Lukin S, Kulcsár MJ, Žilić D, Cetina M, Halasz I, Raić-Malić S, Užarević K. Beilstein J Org Chem 2017; 13: 2352-2363.
| Crossref |

79 Shirai A, Miyata O, Tohnai N, Miyata M, Procter DJ, Sucunza D, Naito T. J Org Chem 2008; 73: 4464-4475.
| Crossref |

80 Poulsen TB, Jørgensen KA. Chem Rev 2008; 108: 2903-2915.
| Crossref |

81 Ballini R, Palmieri A, Petrini M, Torregiani E. Org Lett 2006; 8: 4093-4096.
| Crossref |

82 Jiang R, Wu X-J, Zhu X, Xu X-P, Ji S-J. Eur J Org Chem 2010; 2010: 5946-5950.
| Crossref |

83 Bandini M, Melloni A, Tommasi S, Umani-Ronchi A. Synlett 2005; 2005: 1199-1222.
| Crossref |

84 Terrasson V, Marcia de Figueiredo R, Campagne JM. Eur J Org Chem 2010; 2010(14): 2635-2655.
| Crossref |

85 Galli C, Mandolini L. Eur J Org Chem 2000; 2000: 3117-3125.
| Crossref |

86 Katritzky AR, Xu Y-J, He H-Y. J Chem Soc, Perkin Trans 1 2002; 2002(5): 592-598 598.
| Crossref |

87 Reiter M, Torssell S, Lee S, MacMillan DWC. Chem Sci 2010; 1: 37-42.
| Crossref |

88 De Simone F, Andrès J, Torosantucci R, Waser J. Org Lett 2009; 11: 1023-1026.
| Crossref |

89 Oniciu DC. Eight‐membered rings with one nitrogen atom. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK, editors. Comprehensive Heterocyclic Chemistry III. New York, NY, USA: Pergamon Press; 2008. Vol. 14, pp. 1–47,

90 Dethe DH, Erande RD, Ranjan A. J Am Chem Soc 2011; 133: 2864-2867.
| Crossref |

91 Stang EM, White MC. J Am Chem Soc 2011; 133: 14892-14895.
| Crossref |

92 Takayama Y, Yamada T, Tatekabe S, Nagasawa K. Chem Commun 2013; 49: 6519-6521.
| Crossref |

93 Osante I, Collado MI, Lete E, Sotomayor N. Eur J Org Chem 2001; 2001: 1267-1277.
| Crossref |

94 Li S, Chiu P. Tetrahedron Lett 2008; 49: 1741-1744.
| Crossref |

95 Auerbach J, Weinreb SM. J Am Chem Soc 1972; 94: 7172-7173.
| Crossref |

96 Hazebroucq G, Gardent J. C R Acad Sci 1963; 257: 923-9235.

97 Dolby LJ, Nelson SJ, Senkovich D. J Org Chem 1972; 37: 3691-3695.
| Crossref |

98 Yonemitsu O, Okuno Y, Kanaoka Y, Witkop B. J Am Chem Soc 1970; 92: 5686-5690.
| Crossref |

99 Abd El-Aal HAK, Khalaf AA. Chem Heterocycl Comp 2019; 55: 632-643.
| Crossref |

100 Abd El-Aal HAK, Khalaf AA. Aust J Chem 2019; 72: 276-287.
| Crossref |

101 Abd El-Aal HAK. Arkivoc 2018; 2018(iii): 45-61.
| Crossref |

102 Abd El-Aal HAK. Aust J Chem 2017; 70: 1082-1092.
| Crossref |

103 Abd El-Aal HAK, Khalaf AA. Arkivoc 2019; 2019(v): 265-278.
| Crossref |

104 Abd El-Aal HAK, Khalaf AA, El-Khawaga AMA. J Heterocyclic Chem 2014; 51: 262-268.
| Crossref |

105 Abd El-Aal HAK. Chem Heterocycl Comp 2020; 56: 1353-1362.
| Crossref |

106 Arbačiauskienė E, Martynaitis V, Krikštolaitytė S, Holzer W, Šačkus A. Arkivoc 2011; 2011(xi): 1-21.
| Crossref |

107 La Regina G, Gatti V, Piscitelli F, Silvestri R. ACS Comb Sci 2011; 13: 2-6.
| Crossref |

108 Meth-Cohn O, Stanforth SP. Comp Org Syn 1991; 2: 777-794.

109 Kinastowski S, Nowacki A. Tetrahedron Lett 1982; 23: 3723-3724.
| Crossref |

110 Silverstein RM, Webster FX, Kiemle DJ. Spectrometric Identification of Organic Compounds, 7th edn. Hoboken, NJ, USA: Wiley; 2005.

111 Larock R. Comprehensive Organic Transformations, 2nd edn. New York, NY, USA: Wiley-VCH; 1999. pp. 1422–1433.

112 Huang A, Liu X, Li L, Wu X, Liu W, Liang Y. Adv Synth Catal 2004; 346: 599-602.
| Crossref |

113 Olah GA, Mathew T, Farnia M, Prakash GKS. Synlett 1999; 1999: 1067-1068.
| Crossref |

114 March J. Advanced Organic Chemistry, 4th edn. New York, NY, USA: Wiley; 2000.

115 Répichet S, Le Roux C, Dubac J, Desmurs J-R. Eur J Org Chem 1998; 1998: 2743-2746.
| Crossref |

116 Pearson DE, Buehler CA. Synthesis 1972; 1972: 533-542.
| Crossref |

117 Popp FD, McEwen WE. Chem Rev 1958; 58: 321-401.
| Crossref |

118 Yamato T, Hideshima C, Prakash GKS, Olah GA. J Org Chem 1991; 56: 3955-3957.
| Crossref |

119 Brunette SR, Lipton MA. J Org Chem 2000; 65: 5114-5119.
| Crossref |

120 Huffman JW, Smith VJ, Padgett LW. Tetrahedron 2008; 64: 2104-2112.
| Crossref |

121 Olah GA, Kobayashi S. J Am Chem Soc 1971; 93: 6994.

122 Anderson HJ, Loader. CE, Xu RX, Lê N, Gogan NJ, McDonald R, Edwards LG. Can J Chem 1985; 63: 896-902.
| Crossref |

Synthesis of naphtho- and pyrazolo-fused systems by an intramolecular Friedel–Crafts approach

Abstract

References

Subscriber Login