Silicon-Induced General, Mild, and Efficient One-Pot, Three-Component Synthesis of Amidoalkyl Naphthol Libraries

Abstract

A general mild and efficient protocol for the synthesis of amidoalkyl naphthol libraries was achieved utilizing tetrachlorosilane and zinc chloride in dichloromethane at ambient temperature via a one-pot, three-component condensation of various aldehydes, nitriles (amides), and β-naphthol.

Key words

multicomponent reactions - amidoalkyl naphthols - ­tetrachlorosilane - Ritter reaction - combinatorial synthesis

• References and Notes

• 1a Seebach D, Matthews JL. J. Chem. Soc., Chem. Commun. 1997; 2015
• 1b Wang Y.-F, Izawa T, Kobayashi S, Ohno M. J. Am. Chem. Soc. 1982; 104: 6465
• 1c Knapp S. Chem. Rev. 1995; 95: 1859
• 1d Juaristi E In Enantioselective Synthesis of β-Amino Acids . Juaristi E. John Wiley and Sons; New York: 1997
• 2 Damodiran M, Selvam NP, Perumal PT. Tetrahedron Lett. 2009; 50: 5474
• 3a Dingermann T, Steinhilber D, Folkers G In Molecular Biology in Medicinal Chemistry . Wiley-VCH; Weinheim: 2004
• 3b Shen AY, Tsai CT, Chen CL. Eur. J. Med. Chem. 1999; 877
• 3c Shen AY, Chen CL, Lin CI. Chin. J. Physiol. 1992; 35: 45
• 3d Szatmari I, Fülop F. Curr. Org. Synth. 2004; 1: 155
• 4 Abou-Elmagd WS. I, Hashem AI. Med. Chem. Res. 2013; 22: 2005
• 5a For a review, see: Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
• 5b Thomson LA, Ellman JA. Chem. Rev. 1996; 96: 555
• 5c Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopala L. Acc. Chem. Res. 2003; 36: 899
• 5d Hulme C, Gore V. Curr. Med. Chem. 2003; 10: 51
• 6a PTSA: Khodaei MM, Khosropour AR, Moghanian H. Synlett 2006; 916
• 6b P₂O₅: Nandi GC, Samai S, Kumar R, Singh MS. Tetrahedron Lett. 2009; 50: 7220
• 6c [TEBSA][HSO₄] Bronsted acidic ionic liquid: Hajipour AR, Ghayeb Y, Sheikhan N, Ruoho AE. Tetrahedron Lett. 2009; 50: 5649
• 6d Thiamine hydrochloride: Lei M, Ma L, Hu L. Tetrahedron Lett. 2009; 50: 6393
• 6e Yb(OTf)₃ in ionic liquid: Kumar A, Rao MS, Ahmad I, Khungar B. Can. J. Chem. 2009; 87: 714
• 6f H₃Mo₁₂O₄₀P: Gawand P, Deokar H, Langi B, Yadav A, Chaskar A. Synth. Commun. 2009; 39: 4171
• 6g Ferrocene-labeled supported ionic liquid phase: Rashinkar G, Salunkhe R. J. Mol. Catal. A: Chem. 2010; 316: 146
• 6h Silica gel supported dual acidic ionic liquid: Zhang Q, Luo J, Wei Y. Green Chem. 2010; 12: 2246
• 6i [TBBDA]: Ghorbani-Vaghei R, Malaekehpour SM. Cent. Eur. J. Chem. 2010; 8: 1086
• 6j PEG-based dicationic acidic ionic liquids: Lue J, Zhang Q. Monatsh. Chem. 2011; 142: 923
• 6k Copper p-toluenesulfonate: Wang M, Liang Y. Monatsh. Chem. 2011; 142: 153
• 6l Copper o-toluenesulfonate: Zhigue S, Shuang Z, Xin W. Chin. J. Org. Chem. 2011; 31: 870
• 6m 1,3-Dibromo-5,5-dimethylhydantoin: Habibzadeh S, Ghasemnejad-Bosra H. J. Chin. Chem. Soc. 2011; 58: 1
• 6n Silica gel supported ionic liquid: Kotadia DA, Soni SS. J. Mol. Catal. A: Chem. 2011; 353-354: 44
• 6o Nanosulfated zirconia: Zali A, Shokrolahi A. Chin. Chem. Lett. 2012; 23: 269
• 6p Ethylammonium nitrate ionic liquid: Mulla SA. R, Salama TA, Pathan MY, Inamdar SM, Chavan SS. Tetrahedron Lett. 2013; 54: 672
• 7 Selvam NP, Perumal PT. Tetrahedron Lett. 2006; 47: 7481
• 8 Shaterian HR, Yarahmadi H, Ghashang M. Tetrahedron 2008; 64: 1263
• 9 Shaterian HR, Yarahmadi H. Tetrahedron Lett. 2008; 49: 1297
• 10a Shaterian HR, Yarahmadi H. ARKIVOC 2008; (ii): 105
• 10b Khazaei A, Moosavi-Zare AR, Zare A, Parhami A, Khalafi-Nezhad AK. Appl. Catal., A 2010; 386: 179
• 10c Das B, Laxminarayana K, Thirupathi PR. Synlett 2007; 3103
• 11 Silvam NP, Perumal PT. Tetrahedron 2008; 64: 2972
• 12 Tamaddon F, Bistgani JM. Synlett 2011; 2947
• 13a Salama TA, Ismail MA, Khalil AM, Elmorsy SS. ARKIVOC 2012; (ix): 242
• 13b Salama TA, Novak Z. Tetrahedron Lett. 2011; 52: 40263
• 13c Salama TA, Elmorsy SS, Khalil AM, Ismail MA. Chem. Lett. 2011; 40: 1149
• 13d Salama TA, Elmorsy SS. Chin. Chem. Lett. 2011; 22: 1171
• 13e Salama TA, El-Ahl AS, Elmorsy SS, Khalil AM, Ismail MA. Tetrahedron Lett. 2009; 50: 5933
• 13f Salama TA, Elmorsy SS, Khalil AM, Ismail MA. Tetrahedron Lett. 2007; 48: 6199
• 13g Salama TA, Elmorsy SS, Khalil AM. Tetrahedron Lett. 2007; 48: 4395
• 13h Salama TA, Elmorsy SS, Khalil AM, Girges MM, El-Ahl AS. Synth. Commun. 2007; 37: 1313
• 13i Salama TA, El-Ahl AS, Khalil AM, Girges MM, Lackner B, Steindl C, Elmorsy SS. Monatsh. Chem. 2003; 134: 1241
• 13j Elmorsy SS, Khalil AM, Girges MM, Salama TA. Tetrahedron Lett. 1997; 38: 1071
• 13k Elmorsy SS, Khalil AM, Girges MM, Salama TA. J. Chem. Res., Synop. 1997; 231
• 14a Al-Hourani BJ, Sharma SK, Suresh M, Wuest F. Bioorg. Med. Chem. Lett. 2012; 22: 2235
• 14b Shimoda Y, Kotani S, Sugiura M, Nakajima M. Chem. Eur. J. 2011; 17: 7992
• 14c Rossi S, Benaglia M, Genoni A, Benincori T, Celentano G. Tetrahedron 2011; 67: 158
• 14d Kashiwagi T, Kotani S, Sugiura M, Nakajima M. Tetrahedron 2011; 67: 531
• 14e Khatab TK, El-Bayouki KA. M, Basyouni WM. Tetrahedron Lett. 2011; 52: 1448
• 14f Azizi N, Bagh R, Ghafuri H, Bolourtchian M, Hashemi M. Synlett 2010; 379
• 14g He Y, Bian Z, Kang C, Cheng Y, Gao L. Tetrahedron 2010; 66: 3553
• 14h Sato S, Hoshino H, Sugimoto T, Kashiwagi K. Chem. Lett. 2010; 39: 1319
• 14i El-Deeb IM, Lee SH. Bull. Korean Chem. Soc. 2010; 31: 1757
• 14j Malkov AV, Gordon MR, Stonius S, Hussain J, Koovsk P. Org. Lett. 2009; 11: 5390
• 15 Merijan A, Gardner PD. J. Org. Chem. 1965; 30: 3965
• 16a Zaugg HE. Synthesis 1984; 85
• 16b Zaugg HE. Synthesis 1984; 181
• 16c Katritzky AR, Fang Y, Silina A. J. Org. Chem. 1999; 64: 7622
• 17a Yamamoto Y, Onuki S, Yumoto M, Asao N. J. Am. Chem. Soc. 1994; 116: 421
• 17b Yamamoto Y, Onuki S, Yumoto M, Asao N. Heterocycles 1998; 47: 765
• 18a Nakamura E, Aoki S, Sekiya K, Oshino H, Kuwajima I. J. Am. Chem. Soc. 1987; 109: 8056
• 18b Sakurai H, Sasaki K, Hosomi A. Tetrahedron Lett. 1981; 22: 745
• 19a Zimmerman HE, Traxler MD. J. Am. Chem. Soc. 1957; 79: 1920
• 19b Wessjohann L, Wilde H. Synlett 1997; 731
• 20 Lora-Tamayo M, Madronero R, Muñoz GG, Leipprand H. Chem. Ber. 1964; 97: 2234
• 21 Icrimen LI, Cota DK. Org. React. 1969; 17: 213
• 22 Typical Procedure for the MCR of Compounds 1–3 with SiCl₄/ZnCl₂ To a solution of anhyd ZnCl₂ (0.7 g, 5 mmol) in CH₂Cl₂ (20 mL) were added aldehyde (5 mmol), 2-naphthol (5 mmol), and nitrile or amide (6.5 mmol). The reaction mixture was stirred at ambient temperature for 10 min, SiCl₄ (1.2 mL, 10 mmol) was added, and the reaction mixture was stirred with exclusion of moisture. On completion (TLC monitoring of the progress of the reaction), the mixture was poured onto H₂O (100 mL) and extracted with CH₂Cl₂ (2 × 50 mL). The combined organic extract was dried over anhyd MgSO₄, evaporated, and the residue chromatographed on silica gel using PE–EtOAc (1:1 for 4–6 and 2:1 for 7–10) as eluent to give pure 1-amidoalkyl naphthols. Compounds 6a–d were isolated without chromatography in pure form by trituration with Et₂O. Spectral data for representative (new) examples of 1-amidoalkyl naphthols are shown in the Supporting Information.