MCPBA-Promoted Tandem Michael Addition–Intramolecular Cyclization of 2-Azido-β-amino Esters: Single Pot, Convenient Access to 1,2,4,5-Tetrasubstituted Imidazoles

Raghu Raj; M. S. Hundal; Vipan Kumar

doi:10.1055/s-0033-1338656

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(14): 2054-2058
DOI: 10.1055/s-0033-1338656

letter

MCPBA-Promoted Tandem Michael Addition–Intramolecular Cyclization of 2-Azido-β-amino Esters: Single Pot, Convenient Access to 1,2,4,5-Tetrasubstituted Imidazoles

Raghu Raj

Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com

,

M. S. Hundal

Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com

,

Vipan Kumar*

Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com

› Institutsangaben

Abstract

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Abstract

A simple, single-pot synthesis of tetrasubstituted imidazoles has been developed through the use of MCPBA-promoted tandem Michael addition–intramolecular cyclization of 2-azido-β-amino esters.

Key words

multicomponent reactions - small ring systems - Michael addition - intramolecular cyclization - imidazoles

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Referenzen

References and Notes
1 Blank JW, Durant GJ, Emmett JC, Ganellin CR. Nature 1974; 248: 65
2 Chary MV, Keerthysri NC, Vupallapati SV. N, Lingaiah N, Kantevari S. Catal. Commun. 2008; 9: 2013
3 Ballard SA, Lodola A, Tarbit MH. Biochem. Pharmacol. 1988; 37: 4643
4 Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A. Bioorg. Med. Chem. Lett. 1999; 9: 1023
5 Hranjec M, Piantanida I, Kralj M, Šuman L, Pavelić K, Karminski-Zamola G. J. Med. Chem. 2008; 51: 4899
6 Venkatesan S, Meera KM, Begum S. Desalination 2009; 236: 65
7 Gupta P, Hameed S, Jain R. Eur. J. Med. Chem. 2004; 39: 805
8 Lee JC, Laydon JT, McDonnell PC, Gallagher TF, Kumar S, Green D, McNulty D, Blumenthal MJ, Keys JR, Vatter SW. L, Strickler JE, McLaughlin MM, Siemens IR, Fisher SM, Livi GP, White JR, Adams JL, Young PR. Nature 1994; 372: 739
9 Takle AK, Brown MJ. B, Davies S, Dean DK, Francis G, Gaiba A, Hird AW, King FD, Lovell PJ, Naylor A, Reith AD, Steadman JG, Wilson DM. Bioorg. Med. Chem. Lett. 2006; 16: 378
10 De Laszlo SE, Hacker C, Li B, Kim D, MacCoss M, Mantalo N, Pivnichny JV, Colwell L, Koch GE, Cascieri MA, Hagmenn WK. Bioorg. Med. Chem. Lett. 1999; 9: 641
11 Schmierer R, Mildenberger H, Buerstell H. German Patent 361464, 1987 ; Chem. Abstr. 1988, 108, 37838
12 Omotowa BA, Shreeve JM. Organometallics 2004; 23: 783
13 Alonen A, Jansson J, Kallonen S, Kiriazis A, Aitio O, Finel M, Kostiainen R. Bioorg. Med. Chem. 2008; 36: 148
14 Lindberg P, Nordberg P, Alminger T, Brandstorm A, Wallmark B. J. Med. Chem. 1986; 29: 1327

15a Koike H, Konse T, Sada T, Ikeda T, Hyogo A, Hinman D, Saito H, Yanagisawa H. Ann. Rep. Sankyo Res. Lab. 2003; 55: 1
15b Abrahams SL, Hazen RJ, Batson AG, Phillips AP. J. Pharmacol. Exp. Ther. 1989; 249: 359
15c Leister C, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453

16 Polevaya L, Mavromoustakos T, Zoumboulakis P, Grdadolnik SG, Roumelioti P, Giatas N, Mutule I, Keivish T, Vlahakos DV, Iliodromitis EK, Kremastinos DT, Matsoukas J. Bioorg. Med. Chem. 2001; 9: 1639
17 Grange RL, Ziogas J, North AJ, Angus JA, Schiesser CH. Bioorg. Med. Chem. Lett. 2008; 18: 1241
18 Mannhold R. Drugs Future 1985; 10: 570

19a Diez-Gonzalez S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
19b Poyatos M, Mata JA, Peris E. Chem. Rev. 2009; 109: 3677
19c Benhamou L, Chardon E, Lavigne G, Bellemin-Laponnaz S, Cesar V. Chem. Rev. 2011; 111: 2705

20a Pinkert A, Marsh KN, Pang SS, Staiger MP. Chem. Rev. 2009; 109: 6712
20b Martins MA. P, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG. Chem. Rev. 2008; 108: 2015

21a Zhang Z, Xie F, Jia J, Zhang W. J. Am. Chem. Soc. 2010; 132: 15939
21b Ding H, Ma C, Yang Y, Wang Y. Org. Lett. 2005; 7: 2125
21c Hojabri L, Hartikka A, Moghaddam FM, Arvidsson PI. Adv. Synth. Catal. 2007; 349: 740

22a Zhu H.-J, Wang J.-S, Patrick KS, Donovan JL, DeVane CL, Markowitz JS. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2007; 858: 91
22b Kuroda N, Shimoda R, Wada M, Nakashima K. Anal. Chim. Acta 2000; 403: 131
22c Nakashima K, Yamasaki H, Kuroda N, Akiyama S. Anal. Chim. Acta 1995; 303: 103

23 Staehelin M, Burland DM, Ebert M, Miller RD, Smith BA, Twieg RJ, Volksen W, Walsh CA. Appl. Phys. Lett. 1992; 61: 1626

24a Balalaie S, Arabanian A. Green Chem. 2002; 2: 274
24b Kidwai M, Mothsra P, Bansal V, Somvanshi RK, Ethayathulla AS, Dey S, Singh TP. J. Mol. Catal. A: Chem. 2007; 265: 177
24c Kantevari S, Vuppalapati SV. N, Biradar DO, Nagarapu L. J. Mol. Catal. A: Chem. 2007; 266: 109
24d Heravi MM, Derikvand F, Bamoharram FF. J. Mol. Catal. A: Chem. 2007; 263: 112
24e Nagarapu L, Apuri S, Kantevari S. J. Mol. Catal. A: Chem. 2007; 266: 104
24f Karimi AR, Alimohammadi Z, Azizian J, Mohammadi AA, Mohammadizadeh MR. Catal. Commun. 2006; 7: 728

25 Samai S, Nandi GC, Singh P, Singh MS. Tetrahedron 2009; 65: 10155
26 Heravi MM, Derikvand F, Haghighi M. Monatsh. Chem. 2008; 139: 31
27 Sadeghi B, Mirjalili BB. F, Hashemi MM. Tetrahedron Lett. 2008; 49: 2575
28 Zhang C, Moran EJ, Woiwade TF, Short KM, Mjalli AM. M. Tetrahedron Lett. 1996; 37: 751
29 Claiborne CF, Liverton NJ, Nguyen KT. Tetrahedron Lett. 1998; 39: 8939
30 Karimi AR, Alimohammadi Z, Amini MM. Mol. Diversity 2010; 14: 635

31a Balalaie S, Hashemi MM, Akhbari M. Tetrahedron Lett. 2003; 44: 1709
31b Lantos I, Zhang W.-Y, Shui X, Eggleston DS. J. Org. Chem. 1993; 58: 7092
31c Davidson D, Weiss M, Jelling M. J. Org. Chem. 1937; 2: 319

32 Georg GI. The Organic Chemistry of β-Lactams. VCH; New York, NY: 1992. and references cited therein

33a Ojima I, Shimizu N, Qiu X, Chen H.-JC, Nakahashi K. Bull. Soc. Chim. Fr. 1987; 649
33b Hatanaka N, Abe R, Ojima I. Chem. Lett. 1981; 10: 1297
33c Ojima I. Acc. Chem. Res. 1995; 28: 383
33d Xu J. Tetrahedron 2012; 68: 10696

34a Deshmukh AR, Bhawal BM, Krishnaswamy D, Govande VV, Shinkre BA, Jayanthi A. Curr. Med. Chem. 2004; 11: 1889
34b Alcaide B, Almendros P. Curr. Med. Chem. 2004; 11: 1921
34c Palomo C, Aizpurua JM, Ganboa I, Oiardide M. Curr. Med. Chem. 2004; 11: 1837
34d Alcaide B, Almendros P, Cabrero G, Ruiz MP. Chem. Commun. 2007; 4788
34e Kamath A, Ojima I. Tetrahedron 2012; 68: 10640
34f Dekeukeleire S, D’hooghe M, Vanwalleghem M, Brabandt WV, De Kimpe N. Tetrahedron 2012; 68: 10827

35 Singh P, Mehra V, Anand A, Kumar V, Mahajan MP. Tetrahedron Lett. 2011; 52: 5060

36a Kumar K, Kumar S, Singh T, Anand A, Kumar V. Tetrahedron Lett. 2014; DOI: 10.1016/j.tetlet.2014.05.016
36b Mehra V, Kumar V. Tetrahedron Lett. 2014; 55: 845
36c Mehra V, Singh P, Manhas N, Kumar V. Synlett 2014; 29: 1124
36d Mehra V, Kumar V. Tetrahedron 2013; 69: 3857
36e Mehra V, Neetu Kumar V. Tetrahedron Lett. 2013; 54: 4763
36f Mehra V, Kumar V. Tetrahedron Lett. 2013; 54: 6041
36g Raj R, Mehra V, Singh P, Kumar V, Bhargava G, Mahajan MP, Handa S, Slaughter L. Eur. J. Org. Chem. 2011; 2697

37 Synthesis of 1-Aryl/Alkyl-2,5-distyryl-1H-imidazole-4-carboxylic Acid Methyl Ester 4; General Procedure: To a stirred solution of β-amino esters 2 and 3 (1 mmol) in anhydrous chloroform, MCPBA (1.5 mmol) was added and the reaction mixture was heated to reflux for 10–12 h. The progress of the reaction was monitored by TLC analysis. Upon completion, the reaction was quenched with water (20 mL) and extracted with chloroform (2 × 50 mL). The combined organic layers were dried over anhydrous Na₂SO₄, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate–hexane, 15:85) to afford 4 in good to excellent yield. 2,5-Distyryl-1-p-tolyl-1H-imidazole-4-carboxylic Acid Methyl Ester (4a): Pale-yellow solid; m.p. 122-123 °C; IR (KBr): 1617 cm^–1; ¹H NMR (300 MHz, CDCl₃): δ = 2.52 (s, 3 H, CH₃), 4.00 (s, 3 H, OCH₃), 6.47 (d, J = 16.2 Hz, 2 H, olefinic-H), 7.24–7.41 (m, 14 H, ArH), 7.52 (d, J = 16.5 Hz, 1 H, olefinic-H), 7.74 (d, J = 15.9 Hz, 1 H, olefinic-H); ¹³C NMR (125 MHz, CDCl₃): δ = 21.4, 52.0, 113.0, 114.6, 126.6, 127.0, 128.0, 128.2, 128.5, 128.6, 128.7, 130.2, 130.7, 133.3, 133.4, 135.1, 136.1, 136.7, 136.9, 140.2, 147.2, 164.1; HRMS (ESI-micrOTOF-QII): m/z [M + H]⁺ calcd for C₂₈H₂₄N₂O₂: 421.1838; found: 421.1847. Anal. Calcd (%) for C₂₈H₂₄N₂O₂: C, 79.98; H, 5.75; N, 6.66. Found: C, 80.12, H, 5.68, N, 6.77. X-ray Crystal Data and Structure Refinement for 4a: C₂₈H₂₄N₂O₂; monoclinic; space group P 21/c; a = 11.293 (4) Å, b = 7.318 (2) Å, c = 26.722 (9) Å, α = 90°, β = 95.244 (14)°, γ = 90°; V = 2199.1 (12) Å³; Z = 4; D calcd. = 1.270 g/cm³; μ = 0.080 mm^–1, T = 100 (2) K; 2θ max = 27.61°, completeness to 2θ max = 99.4%, total reflections = 19830, independent (Rint = 0.1590), 5080 observed [I>2σ(I)]. Final R1 [I>2σ(I)] = 0.0732, wR2 (all data) = 0.1752, largest difference peak and hole 0.313 and –3.15 e.Å^–3. X-ray intensity data were obtained with a Bruker Apex-II CCD diffractometer using Mo K_α (λ = 0.71069 Å). The data were processed by SAINT. Lorentz and polarization effects and empirical corrections were applied by using SADABS from Bruker. CCDC-998758 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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