Synthesis 2016; 48(23): 4221-4227
DOI: 10.1055/s-0035-1560562
paper
© Georg Thieme Verlag Stuttgart · New York

Photoinduced Aromatization of Dihydropyridines

Zheng Lu*
School of Pharmacy, Jiangsu University, Zhenjiang, Jiangsu 212013, P. R. of China   Email: lz@ujs.edu.cn   Email: yqy@ujs.edu.cn
,
Yong-Qing Yang*
School of Pharmacy, Jiangsu University, Zhenjiang, Jiangsu 212013, P. R. of China   Email: lz@ujs.edu.cn   Email: yqy@ujs.edu.cn
,
Hong-Xia Li
School of Pharmacy, Jiangsu University, Zhenjiang, Jiangsu 212013, P. R. of China   Email: lz@ujs.edu.cn   Email: yqy@ujs.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 13 May 2016

Accepted after revision: 13 July 2016

Publication Date:
26 August 2016 (online)


Dedicated to Professor Xiyan Lu on the occasion of his 88th birthday

Abstract

The combination of tris(bipyridine)ruthenium(II)/visible light/air is found to be effective for the aromatization of many dihydropyridines. A low catalyst loading of just 0.02 mol% is required.

Supporting Information

 
  • References

  • 1 Pollak N, Dölle C, Ziegler M. Biochem. J. 2007; 402: 205
  • 2 Elliott WJ, Ram VS. J. Clin. Hypertens. 2011; 13: 687
    • 3a Wang B, Hu Y, Hu H. Synth. Commun. 1999; 29: 4193
    • 3b Merarian HR, Mohammadpoor-Baltork I, Javahery M. J. Chin. Chem. Soc. 2006; 53: 511
    • 3c Zolfigol MA, Salehi P, Ghorbani-Chogharmarani A, Safaiee M, Shahamirian M. Synth. Commun. 2007; 37: 1817
    • 4a García O, Delgado F, Cano AC, Alvarez C. Tetrahedron Lett. 1993; 34: 623
    • 4b Ghorbani-Choghamarani A, Zeinivand J. Synth. Commun. 2010; 40: 2457
  • 5 Lu J, Bai Y, Wang Z, Yang B, Li W. Synth. Commun. 2001; 31: 2625
  • 6 Saikh F, De R, Ghosh S. Tetrahedron Lett. 2014; 55: 6171
    • 7a Nasr-Esfahani M, Moghadam M, Tangestaninejad S, Mirkhani V. Bioorg. Med. Chem. Lett. 2005; 15: 3276
    • 7b Nasr-Esafahani M, Moghadam M, Tangestanienejad S, Mirkhani V, Momeni AR. Bioorg. Med. Chem. 2006; 14: 2720
    • 7c Karade NN, Gampawar SV, Kondre JM, Shide SV. ARKIVOC 2008; (xii): 9
    • 7d Montazerozohori M, Nasr-Esfahani M, Joohari S, Haghighat N. Asian J. Chem. 2010; 22: 4249
    • 8a Hashemi MM, Ahmadibeni Y, Ghafuri H. Monatsh. Chem. 2003; 134: 107
    • 8b Chen ZY, Zhang W. Chin. Chem. Lett. 2007; 18: 1443
    • 8c Pardeshi SK, Kumbhar DD, Waghamare BY. J. Indian Counc. Chem. 2008; 25: 90
    • 8d Kumar A, Maurya RA, Sharma S. Bioorg. Med. Chem. Lett. 2009; 19: 4432
    • 8e Su J, Zhang C, Lin D, Duan Y, Fu X, Mu R. Synth. Commun. 2010; 40: 595
    • 8f Hatamjafari F, Montazeri N, Pourshamsian K. Asian J. Chem. 2011; 23: 3287
    • 8g Shi L.-X, Zaho W.-F, Xu X, Tang J, Wu C.-D. Inorg. Chem. 2011; 50: 12387
    • 8h Sharbatdaran M, Jafari Foruzin L, Farzaneh F, Larijani MM. C. R. Chim. 2013; 16: 176
    • 8i Safaiee M, Zolfigol MA, Tavasoli M, Mokhlesi M. J. Iran. Chem. Soc. 2014; 11: 1593
    • 8j Jalalian M, Farzaneh F, Foruzin LJ. J. Cluster Sci. 2015; 26: 703
  • 9 Gorjizadeh M, Abdollahi-Alibeik M. Chin. Chem. Lett. 2011; 22: 61
  • 10 Pfister JR. Synthesis 1990; 689
  • 11 Pragst F, Kaltofen B, Volke J, Kuthan J. J. Electroanal. Chem. 1981; 119: 301
    • 12a Mashraqui SH, Karnik MA. Tetrahedron Lett. 1998; 39: 4895
    • 12b Nakamichi N, Kawashita Y, Hayashi M. Org. Lett. 2002; 4: 3955
    • 12c Wang D.-L, Liu Q, Chen B, Zhang L.-P, Tung C.-H, Wu L.-Z. Chin. Sci. Bull. 2010; 55: 2855
    • 12d Chen S, Hossain MS, Foss FW. Jr. ACS Sustainable Chem. Eng. 2013; 1: 1045
  • 13 Liao X, Lin W, Lu J, Wang C. Tetrahedron Lett. 2010; 51: 3859
  • 14 Mirza-Aghayan M, Boukherroub R, Nemati M, Rahimifard M. Tetrahedron Lett. 2012; 53: 2473
    • 15a Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
    • 15b Larraufie M.-H, Pellet R, Fensterbank L, Goddard J.-P, Lacôte E, Malacria M, Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
    • 15c Yang D.-T, Meng Q.-Y, Zhong J.-J, Xiang M, Liu Q, Wu L.-Z. Eur. J. Org. Chem. 2013; 7528
    • 15d Cismesia MA, Ischay MA, Yoon TP. Synthesis 2013; 45: 2699
    • 15e Pratsch G, Overman LE. J. Org. Chem. 2015; 80: 11388
    • 15f Speckmeier E, Padie C, Zeitler K. Org. Lett. 2015; 17: 4818
    • 15g Jana A, Mondal J, Borah P, Mondal S, Bhaumik A, Zhao Y. Chem. Commun. 2015; 51: 10746
  • 16 Yang Y.-Q, Lu Z. Chin. J. Chem. 2014; 32: 650
  • 17 A household blue LED bulb was used.
  • 18 Logan BK. J. Chromatogr. 1990; 529: 175
  • 19 A control experiment showed that neither air nor a photocatalyst was necessary.
  • 20 Wu X, Deng Z, Yan J, Zhang Z, Zhang F, Zhang Z. Ind. Eng. Chem. Res. 2014; 53: 9932
  • 21 Litvic M, Cepanec I, Filipan M, Kos K, Bartolincic A, Druskovic V, Tibi MM, Vinkovic V. Heterocycles 2005; 65: 23
  • 22 Xia J.-J, Wang G.-W. Synthesis 2005; 2379
  • 23 Kumar P. Chin. J. Chem. 2009; 27: 1487
  • 24 All the signals of the 1H NMR spectrum recorded in CDCl3 were split, although the offset of these signals showed consistency with ref. 6. The signals in the spectrum taken in CD3OD were sharp, so the NMR spectrum of this compound in CD3OD is reported.
  • 25 Memarian HR, Bagheri M, Döpp D. Monatsh. Chem. 2004; 135: 833
  • 26 Yáñez C, López-Alarcón C, Camargo C, Valenzuela V, Squella JA, Núñez-Vergara LJ. Bioorg. Med. Chem. 2004; 12: 2459