Anilines as Substrates in Consecutive Four-Component Synthesis of Novel 1-Aryl-5-benzoyl-6-phenyl-3,4-dihydropyridin-2(1H)-ones

Jan Nordmann; Thomas J. J. Müller

doi:10.1055/s-0033-1338574

Synthesis, Table of Contents

Synthesis 2014; 46(04): 522-530
DOI: 10.1055/s-0033-1338574

paper

Anilines as Substrates in Consecutive Four-Component Synthesis of Novel 1-Aryl-5-benzoyl-6-phenyl-3,4-dihydropyridin-2(1H)-ones

Jan Nordmann

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

,

Thomas J. J. Müller*

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

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Abstract

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Dedicated to Prof. Dr. Klaus Theodor Wanner on the occasion of his 60^th birthday

Abstract

The consecutive four-component synthesis of 5-acylpyridin-2(1H)-ones initiated by a copper-free alkynylation in a one-pot fashion has been expanded to include considerably less nucleophilic anilines as the amine component in the Michael addition step by altering the solvent system to 1,4-dioxane; 17 examples for the synthesis of 1-aryl-5-benzoyl-6-phenyl-3,4-dihydropyridin-2(1H)-ones were obtained in moderate to good yields.

Key words

multicomponent reactions - C–C coupling - alkynes - heterocycles - palladium

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References

References

1a Stille JR, Barta NS. Stud. Nat. Prod. Chem. 1996; 18: 315
1b Cook GR, Beholz LG, Stille JR. J. Org. Chem. 1994; 59: 3575
1c Paulvannan K, Stille JR. J. Org. Chem. 1994; 59: 1613
1d Shen W, Coburn CA, Bornmann WG, Danishefsky SJ. J. Org. Chem. 1993; 58: 611
1e Fang FG, Danishefsky SJ. Tetrahedron Lett. 1989; 30: 3621

2 For an example against pulmonary disease, see: Gielen-Haertwig H, Albrecht B, Bauser M, Keldenich J, Volkhart L, Pernerstorfer J, Schlemmer K.-H, Tellan L. US 2008,045,541, 2008

For examples of HIV-1 specific reverse transcriptase inhibitory activities, see:

3a Dolle V, Fan E, Nguyen CH, Aubertin AM, Kirn A, Andreola ML, Jamieson G, Tarragolitvak L, Bisagni E. J. Med. Chem. 1995; 38: 4679
3b Wai JS, Williams TM, Bamberger DL, Fisher TE, Hoffman JM, Hudcosky RJ, MacTough SC, Rooney CS, Saari WS, Thomas CM, Goldman ME, Obrien JA, Emini EA, Nunberg JH, Quintero JC, Schleif WA, Anderson PS. J. Med. Chem. 1993; 36: 249

For examples of 5α-reductase inhibitory activities, see:

4a McCarthy AR, Hartmann RW, Abell AD. Bioorg. Med. Chem. Lett. 2007; 17: 3603
4b Picard F, Schulz T, Hartmann RW. Bioorg. Med. Chem. 2002; 10: 437
4c Hartmann RW, Reichert M, Göhring S. Eur. J. Med. Chem. 1994; 29: 807

5a Hickmott PW, Sheppard G. J. Chem. Soc. C 1971; 65: 1358
5b Hickmott PW, Sheppard G. J. Chem. Soc. C 1971; 65: 2112

6 Barta NS, Brode A, Stille JR. J. Am. Chem. Soc. 1994; 116: 6201
7 Paulvannan K, Stille JR. J. Org. Chem. 1992; 57: 5319

8a Ulanovskaya OA, Cui J, Kron SJ, Kozmin SA. Chem. Biol. 2011; 18: 222
8b d’Angelo J, Cave C, Desmaele D, Gassama A, Thominiaux C, Riche C. Heterocycles 1998; 47: 725
8c Cave C, Gassama A, Mahuteau J, d’Angelo J, Riche C. Tetrahedron Lett. 1997; 38: 4773
8d Von Dobeneck H, Brunner E, Bunke H, Metzner G, Schmidt R, Weil E, Sonnenbichler J. Liebigs Ann. Chem. 1981; 410

9a Alizadeh A, Rezvanian A. Helv. Chim. Acta 2012; 95: 858
9b Chakrabarti S, Panda K, Misra NC, Ila H, Junjappa H. Synlett 2005; 1437
9c Abelman MM, Curtis JK, James DR. Tetrahedron Lett. 2003; 44: 6527
9d Hadden M, Nieuwenhuyzen M, Potts D, Stevenson PJ. J. Chem. Soc., Perkin Trans. 1 1998; 3437

10 Paulvannan K, Chen T. J. Org. Chem. 2000; 65: 6160

11a Lyutenko NV, Gerus II. Tetrahedron Lett. 2013; 54: 4091
11b Ali A, Winzenberg KN. Aust. J. Chem. 2005; 58: 870
11c Cimarelli C, Palmieri G. Tetrahedron 1998; 54: 915
11d Lyubchanskaya VM, Sarkisova LS, Alekseev LM, Granik VG. Pharm. Chem. J. 1994; 28: 70

12a Müller TJ. J. Synthesis 2012; 44: 159
12b Müller TJ. J. Top. Heterocycl. Chem. 2010; 25: 25
12c Willy B, Müller TJ. J. Curr. Org. Chem. 2009; 13: 1777
12d Willy B, Müller TJ. J. ARKIVOC 2008; (i): 195 ; http://www.arkat-usa.org/home
12e D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
12f Müller TJ. J. Targets Heterocycl. Syst. 2006; 10: 54

13a Nordmann J, Breuer N, Müller TJ. J. Eur. J. Org. Chem. 2013; 4303
13b Nordmann J, Müller TJ. J. Org. Biomol. Chem. 2013; 11: 6556

14a Sarma R, Prajapati D. Chem. Commun. 2011; 47: 9525
14b Tsuchimoto T, Hatanaka K, Shirakawa E, Kawakami Y. Chem. Commun. 2003; 2454
14c Chauhan KK, Frost CG. J. Chem. Soc., Perkin Trans. 1 2000; 3015

15a Susanti D, Koh F, Kusuma JA, Kothandaraman P, Chan PW. H. J. Org. Chem. 2012; 77: 7166
15b Zhang Y, Donahue JP, Li C.-J. Org. Lett. 2007; 9: 627
15c Agarwal S, Knölker H.-J. Org. Biomol. Chem. 2004; 2: 3060

16a Luo Y, Li Z, Li C.-J. Org. Lett. 2005; 7: 2675
16b Müller TE. Tetrahedron Lett. 1998; 39: 5961

17a Bhanushali MJ, Nandurkar NS, Bhor MD, Bhanage BM. Catal. Commun. 2008; 9: 425
17b Das B, Chowdhury N. J. Mol. Catal. A: Chem. 2007; 263: 212

18a Rosenfeld DC, Shekhar S, Takemiya A, Utsunomiya M, Hartwig JF. Org. Lett. 2006; 8: 4179
18b Wabnitz TC, Spencer JB. Org. Lett. 2003; 5: 2141

19a Liu J.-R, Fang S, Ding M.-P, Chen Z.-C, Zhou J.-J, Sun F, Jiang B, Huang J. J. Neurol. Sci. 2010; 292: 111
19b Hotchkiss JA, Andrus AK, Johnson KA, Krieger SM, Woolhiser MR, Maurissen JP. Food Chem. Toxicol. 2010; 48: 470
19c Nagano K, Umeda Y, Senoh H, Gotoh K, Arito H, Yamamoto S, Matsushima T. J. Occup. Health 2006; 48: 424

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