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Synlett 2017; 28(09): 1087-1090
DOI: 10.1055/s-0036-1588949
DOI: 10.1055/s-0036-1588949
letter
Multicomponent Cascade Synthesis of 1,4-Dihydropyridine Derivatives from Pyridines, Methyl Propiolate, and Aromatic Acids
Further Information
Publication History
Received: 08 December 2016
Accepted after revision: 22 January 2017
Publication Date:
13 February 2017 (online)
Abstract
A metal-free highly efficient synthesis of a wide range of 4-propenyl 1,4-DHPs from pyridines, methyl propiolate, and aromatic acids is described. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588949.
- Supporting Information
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References and Notes
- 1 Hantzsch A. Ber. 1881; 14: 1637-1637
- 2a Bossert F, Meyer H, Wehinger E. Angew. Chem., Int. Ed. Engl. 1981; 20: 762-762
- 2b Loev B, Goodman M, Snader K, Tedeschi R, Macko E. J. Med. Chem. 1974; 17: 956-956
- 3a Safak C, Simsek R. Mini-Rev. Med. Chem. 2006; 6: 747-747
- 3b Edraki N, Mehdipour AR, Khoshneviszadeh M, Miri R. Drug Discovery Today 2009; 14: 1058-1058
- 3c Mai A, Valente S, Meade S, Carafa V, Tardugno M, Nebbioso A, Galmozzi A, Mitro N, Fabiani ED, Altucci L, Kazantsev A. J. Med. Chem. 2009; 52: 5496-5496
- 3d Schade D, Lanier M, Willems E, Okolotowicz K, Bushway P, Wahlquist C, Gilley C, Mercola M, Cashman JR. J. Med. Chem. 2012; 55: 9946-9946
- 3e Sueki S, Takei R, Zaitsu Y, Abe J, Fukuda A, Seto K, Furukawa Y, Shimizu I. Eur. J. Org. Chem. 2014; 5281-5281
- 4a Hiort J, Maksimenka K, Reichert M, Perović-Ottstadt S, Lin WH, Wray V, Steube K, Schaumann K, Weber H, Proksch P, Ebel R, Müller WE. G, Bringmann G. J. Nat. Prod. 2004; 67: 1532-1532
- 4b Ye YH, Zhu HL, Song YC, Liu JY, Tan RX. J. Nat. Prod. 2005; 68: 1106-1106
- 4c Henrikson JC, Ellis TK, King JB, Cichewicz RH. J. Nat. Prod. 2011; 74: 1959-1959
- 5 Jiang JL, van Rhee AM, Melman N, Ji XD, Jacobson KA. J. Med. Chem. 1996; 39: 4667-4667
- 6 Dondoni A, Massi A, Minghini E, Bertolasi V. Tetrahedron 2004; 60: 2311-2311
- 7a Kwok TC. Y, Ricker N, Fraser R, Chan AW, Burns A, Stanley EF, McCourt P, Cutler SR, Roy PJ. Nature (London, U.K.) 2006; 441: 91-91
- 7b Bisht SS, Dwivedi N, Tripathi RP. Tetrahedron Lett. 2007; 48: 1187-1187
- 7c Kumar S, Sharma P, Kapoor KK, Hundal MS. Tetrahedron 2008; 64: 536-536
- 7d Correa WH, Scott JL. Green Chem. 2001; 3: 296-296
- 7e Maheswara M, Siddaiah V, Rao YK, Tzeng YM, Sridhar C. J. Mol. Catal. A: Chem. 2006; 260: 179-179
- 7f Sharma SD, Hazarika P, Konwar D. Catal. Commun. 2008; 9: 709-709
- 8a Wan JP, Zhou R, Liu Y, Cai M. RSC. Adv. 2013; 3: 2477-2477
- 8b Kang SR, Lee YR. Synthesis 2013; 45: 2593-2593
- 8c Wen LR, Liu C, Li M, Wang LJ. J. Org. Chem. 2010; 75: 7605-7605
- 8d Wan JP, Gan SF, Sun GL, Pan YJ. J. Org. Chem. 2009; 74: 2862-2862
- 8e Yang J, Wang C, Xie X, Li H, Li Y. Eur. J. Org. Chem. 2010; 4189-4189
- 8f Sridhar R, Perumal PT. Tetrahedron 2005; 61: 2465-2465
- 9a Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083-3083
- 9b Wan JP, Liu Y. Synthesis 2010; 3943-3943
- 9c Toure BB, Hall DG. Chem. Rev. 2009; 109: 4439-4439
- 9d D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095-1095
- 9e Ramón DJ, Miguel Y. Angew. Chem. Int. Ed. 2005; 44: 1602-1602
- 9f Orru RV. A, de Greef M. Synthesis 2003; 1471-1471
- 9g Hulme C, Gore V. Curr. Med. Chem. 2003; 10: 51-51
- 9h Zhu JP. Eur. J. Org. Chem. 2003; 1133-1133
- 10 For a review on new MCRs for 1,4-DHPs synthesis, see: Wan JP, Liu Y. RSC Adv. 2012; 2: 9763-9763
- 11 Qin WB, Zhu JY, Kong YB, Bao YH, Chen ZW, Liu LX. Org. Biomol. Chem. 2014; 12: 4252-4252
- 12a Comins DL, King LS, Smith ED, Février FC. Org. Lett. 2005; 7: 5059-5059
- 12b Crotti S, Berti F, Pineschi M. Org. Lett. 2011; 13: 5152-5152
- 12c Katritzky AR, Zhang SM, Kurz T, Wang MY. Org. Lett. 2001; 3: 2807-2807
- 13 General Procedure for the Preparation of (E)-3-Methoxy-2-{1-[(E)-3-methoxy-3- oxoprop-1-en-1-yl]-1,4-dihydropyridin-4-yl}-3-oxoprop-1-en-1-yl benzoate To a solution of pyridine (0.3 mmol) and methyl propiolate (0.72 mmol) in MeCN (1 mL) was added benzoic acid (0.33 mmol) under air atmosphere, and the mixture was stirred at r.t. for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: EtOAc–PE = 1:2) to yield the corresponding product
- 14 Selected Physical and Spectral Data for (E)-3-Methoxy-2-{1-[(E)-3-methoxy-3-oxoprop- 1-en-1-yl]-1,4-dihydropyridin-4-yl}-3-oxoprop-1-en-1-yl benzoate (7a) Yellow amorphous solid; yield: 94 mg (85%). IR (KBr): νmax = 1743, 1706, 1601, 1228, 1153 cm–1. 1H NMR (400 MHz, CDCl3): δ = 8.60 (s, 1 H), 8.07–7.99 (m, 2 H), 7.61 (t, J = 7.5 Hz, 1 H), 7.34–7.25 (m, 2 H), 7.29 (d, J = 13.6 Hz, 1 H), 6.34 (d, J = 7.5 Hz, 2 H), 5.12 (d, J = 13.6 Hz, 1 H), 4.94 (d, J = 4.5 Hz, 2 H), 4.66–4.52 (m, 1 H), 3.80 (s, 3 H, OCH3), 3.73 (s, 3 H, OCH3). 13C NMR (100 MHz, CDCl3): δ = 168.8, 167.1, 162.4, 147.2, 144.3, 134.4, 130.5, 130.3, 128.9, 127.8, 119.9, 108.6, 90.0, 89.2, 52.0, 51.1, 51.0, 31.0. ESI-MS: m/z = 370 (100) [M + H+]. Anal Calcd for C20H19NO6: C, 65.03; H, 5.18; N, 3.79. Found: C, 64.86; H, 5.51; N, 3.64
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