Derivatives of α,α-Aryl Naphthalimide Nitriles as Fluoride Ion Sensors: Convenient Precursors for the Synthesis of Aryl Naphthalimide Ketones

Abstract

A facile and efficient S_NAr procedure involving the displacement of activated naphthalimide bromides with the anions of substituted aryl acetonitriles was developed for the preparation of α,α-aryl naphthalimide nitrile derivatives, which can be used as fluoride ion sensors and convenient precursors for the synthesis of aryl naphthalimide ketones based on fluoride-induced deprotonation followed by autoxidative decyanation.

Key words

substituent effects - supramolecular chemistry - molecular recognition - nucleophilic aromatic substitution - oxidation

• References and Notes

• 1a For leading references, see: Science of Synthesis . Murahashi S.-I. Thieme; Stuttgart: 2004
• 1b Patai S, Friedrich K, Wallenfels K. The Chemistry of the Cyano Group . Wiley-Interscience; New York: 1970
• 1c Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 4442
• 2 Kurz ME, Lapin SC, Mariam KT, Hagen J, Qian XQ. J. Org. Chem. 1984; 2728
• 3 Narsaiah AV, Nagaiah K. Adv. Synth. Catal. 2004; 1271
• 4 Wang GZ, Wu J, Ding K. Org. Lett. 2008; 4573
• 5a Yeung PY, Chung KH, Kwong FY. Org. Lett. 2011; 2912
• 5b Culkin DA, Hartwig JF. Acc. Chem. Res. 2003; 234
• 5c You J, Verkade JG. J. Org. Chem. 2003; 8003
• 5d You J, Verkade JG. Angew. Chem. Int. Ed. 2003; 5051
• 6a Tempesti TC, Pierini AB, Baumgartner MT. New J. Chem. 2012; 597
• 6b Rossi RA, Pierini AB, Peñéñory AB. Chem. Rev. 2003; 71
• 7a Klapars A, Waldman JH, Campos KR, Jensen MS, McLaughlin M, Chung JY, Cvetovich LR. J, Chen C. J. Org. Chem. 2005; 10186
• 7b Sommer MB, Begtrup M, Boegesoe KP. J. Org. Chem. 1990; 4817
• 7c Makosza M, Podraza R, Kwast A. J. Org. Chem. 1994; 6796
• 7d Caron S, Vazquez E, Wojcik JM. J. Am. Chem. Soc. 2000; 712
• 7e Kubota Y, Tsuzuki T, Funabiki K, Ebihara M, Matsui M. Org. Lett. 2010; 4010
• 8a Choi J, Fu GC. J. Am. Chem. Soc. 2012; 9102
• 8b Culkin DA, Hartwig JF. J. Am. Chem. Soc. 2002; 9330
• 9a Qian X, Xiao Y, Xu Y, Guo X, Qian J, Zhu W. Chem. Commun. 2010; 6418
• 9b Liu T, Xu Z, Spring DR, Cui J. Org. Lett. 2013; 2310
• 9c Xu Z, Qian X, Cui J. Org. Lett. 2005; 3029
• 9d Zhang JF, Lim CS, Bhuniya S, Cho BR, Kim JS. Org. Lett. 2011; 1190
• 9e Duke RM, Veale EB, Pfeffer FM, Kruger PE, Gunnlaugsson T. Chem. Soc. Rev. 2010; 3936
• 9f Banerjee S, Veale EB, Phelan CM, Murphy SA, Tocci GM, Gillespie LJ, Frimannsson DO, Kelly JM, Gunnlaugsson T. Chem. Soc. Rev. 2013; 1601
• 9g Lee MH, Kim JY, Han JH, Bhuniya S, Sessler JL, Kang C, Kim JS. J. Am. Chem. Soc. 2012; 12668
• 9h De Los Cobos O, Fousseret B, Lejeune M, Rossignol F, Dutreilh-Colas M, Carrion C, Boissière C, Ribot F, Sanchez C, Cattoën X, Man MW. C, Durand J.-O. Chem. Mater. 2012; 4337
• 9i Yu H, Xiao Y, Jin L. J. Am. Chem. Soc. 2012; 17486
• 9j de Silva AP, Gunaratne HQ. N, Gunnlaugsson T, Huxley AJ. M, McCoy CP, Rademacher JT, Rice TE. Chem. Rev. 1997; 1515
• 10a Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM. J. Med. Chem. 1996; 1201
• 10b Mandal SK, Sarkar A. J. Org. Chem. 1998; 5672
• 10c Taber DF. J. Org. Chem. 2000; 254
• 10d Kobayashi K, Nishimura Y, Gao F, Gotoh K, Nishihara Y, Takagi K. J. Org. Chem. 2011; 1949
• 11 Zhu W, Yao R, Tian H. Dyes Pigm. 2002; 147
• 12 Chen J, Liu C, Zhang J, Ding W, Zhou M, Wu F. Chem. Commun. 2013; 10814
• 13a Yin Z, Zhang Z, Kadow JF, Meanwell NA, Wang T. J. Org. Chem. 2004; 1364
• 13b Ouchi A, Hyugano T, Liu C. Org. Lett. 2009; 4870
• 14a Moragues ME, Martínez-Máñez R, Sancenón F. Chem. Soc. Rev. 2011; 2593
• 14b Wade CR, Broomsgrove AE. J, Aldridge S, Gabbaï FP. Chem. Rev. 2010; 3958
• 14c Zhou Y, Zhang JF, Yoon J. Chem. Rev. 2014; 5511
• 14d Amendola V, Esteban-Gómez D, Fabbrizzi L, Licchelli M. Acc. Chem. Res. 2006; 343
• 14e Gale PA, Busschaert N, Haynes CJ. E, Karagiannidis LE, Kirby IL. Chem. Soc. Rev. 2014; 205
• 14f Lee JY, Cho EJ, Mukamel S, Nam KC. J. Org. Chem. 2004; 943
• 14g Kim T.-H, Swager TM. Angew. Chem. Int. Ed. 2003; 4803
• 14h Du J, Hu M, Fan J, Peng X. Chem. Soc. Rev. 2012; 4511
• 14i Martínez-Máñez R, Sancenón F. Chem. Rev. 2003; 4419
• 14j McDonald KP, Ramabhadran RO, Lee S, Raghavachari K, Flood AH. Org. Lett. 2011; 6260
• 14k Hua Y, Flood AH. Chem. Soc. Rev. 2010; 1262
• 15a Yang Z, Zhang Z, Meanwell NA, Kadow JF, Wang T. Org. Lett. 2002; 1103
• 15b Liu Y, Yun X, Zhang-Negrerie D, Huang J, Du Y, Zhao K. Synthesis 2011; 2984
• 15c Kulp SS, McGee MJ. J. Org. Chem. 1983; 4097
• 16 Typical Procedures Anhydrous THF (25 mL) solution of 2a (0.40 g, 3.42 mmol) was stirred for 1 h at r.t., then N-butyl-4-bromo-1,8-naphthalimide (1, 1.00 g, 3.02 mmol) was added. After completion, the reaction mixture was quenched with HCl (15%) until pH 2–3. The organic fraction was extracted with EtOAc (3 × 20 mL), dried over anhydrous Na₂SO₄, and filtered. Volatile fractions were removed under reduced pressure, and the residual material was purified by flash column chromatography on silica gel (PE–EtOAc, 25:1) to provide 3a as a pink solid 0.80 g (72% yield). 2-{2-Butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}-2-phenylacetonitrile (3a) Yield 0.80 g (72%); mp 140.0–140.1 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.56 (d, J = 7.5 Hz, 1 H), 8.55 (d, J = 6.7 Hz, 1 H), 8.19 (d, J = 8.5 Hz, 1 H), 7.84 (d, J = 7.6 Hz, 1 H), 7.69 (dd, J = 8.3, 7.5 Hz, 1 H), 7.33–7.27 (m, 5 H), 5.83 (s, 1 H), 4.11 (t, J = 7.5 Hz, 2 H), 1.67–1.61 (m, 2 H), 1.41–1.34 (m, 2 H), 0.91 (t, J = 7.4 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 163.8, 163.5, 137.5, 134.2, 131.3, 130.8, 129.6, 129.1, 128.9, 127.9, 127.8, 127.7, 123.7, 118.6, 40.4, 40.3, 30.2, 20.3, 13.8. ESI-HRMS: m/z calcd for C₂₄H₂₁N₂O₂ [M + H]⁺: 369.16030; found: 369.16122. A mixture of compound 3a (0.10 g, 0.27 mmol) and TBAF (0.21g, 0.81 mmol) in CH₂Cl₂ (25 mL) was stirred at r.t. for 6 h. After completion, the solvent was removed under reduced pressure. The residue was subjected to a column chromatography on silica gel (PE–EtOAc, 20:1) to give product 4a as a white solid 92 mg (95% yield). 6-Benzoyl-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (4a) Yield 92 mg (95%); white solid; mp 134.8–135.1 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.58 (d, J = 7.4 Hz, 2 H), 8.27 (d, J = 8.5 Hz, 1 H), 7.78 (d, J = 7.5 Hz, 2 H), 7.74 (d, J = 7.5 Hz, 1 H), 7.69 (dd, J = 8.1, 7.7 Hz, 1 H), 7.59 (dd, J = 7.5, 7.4 Hz, 1 H), 7.43 (dd, J = 7.8, 7.8 Hz, 2 H), 4.14 (t, J = 7.6 Hz, 2 H), 1.70–1.64 (m, 2 H), 1.43–1.36 (m, 2 H), 0.92 (t, J = 7.3 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 196.3, 163.9, 163.6, 141.9, 137.1, 134.1, 131.8, 131.6, 130.4, 129.7, 129.4, 128.8, 128.5, 127.9, 127.3, 124.5, 123.0, 40.4, 30.2, 20.4, 13.8. ESI-HRMS: m/z calcd for C₂₃H₂₀NO₃ [M + H]⁺: 358.14432; found: 358.14605.
• 17 Connors AK. Binding Constants: The Measurement of Molecular Complex Stability. Wiley; New York: 1987