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

Tarek A. Salama

doi:10.1055/s-0032-1318392

Synlett, Table of Contents

Synlett 2013; 24(6): 713-718
DOI: 10.1055/s-0032-1318392

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

Tarek A. Salama

^aChemistry Department, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt Fax: +20(50)2246781 Email: tasalama@yahoo.com

^bDivision of Organic Chemistry, National Chemical Laboratory, Pune 411008, India

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Abstract

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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

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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.

Supplementary Material

Supporting Information