Synthesis 2019; 51(09): 2007-2013
DOI: 10.1055/s-0037-1612058
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Onychines

Mao Arita
a   School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
,
Soichi Yokoyama
a   School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b   Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
,
a   School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b   Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
c   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
,
a   School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b   Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
› Author Affiliations
Further Information

Publication History

Received: 07 November 2018

Accepted after revision: 06 December 2018

Publication Date:
19 February 2019 (online)


Abstract

The FeCl3-mediated condensation of an α-phenylenamino ester and an enone proceeds efficiently to afford a 2-phenylnicotinate. The subsequent intramolecular Friedel–Crafts reaction yielded an ­onychine framework. Modifications at the 2-, 3-, and 8-positions of the onychine framework were easily achieved by altering the enamino esters­ and enones, which facilitated the discovery of potentially bioactive compounds.

Supporting Information

 
  • References

  • 1 De Almeida ME. L, Braz R, Von Bulow MV, Gottlieb OR, Maia JG. S. Phytochemistry 1976; 15: 1186
  • 2 Goulart MO. F, Santana AE. G, De Oliveria AB, De Oliveria GG, Maia JG. S. Phytochemistry 1986; 25: 1691
  • 3 Hufford CD, Liu S, Clark AM, Oguntimein BO. J. Nat. Prod. 1987; 50: 961
  • 4 Koyama J, Sugida T, Suzuta Y, Irie H. Heterocycles 1979; 12: 1017
  • 5 Bowden BF, Picker K, Ritchie E, Taylor WC. Aust. J. Chem. 1975; 28: 2681
  • 6 Leboeuf M, Cavé A. Lloydia 1976; 39: 459
    • 7a Taghavi-Moghadam S, Kwong CD, Secrist JA, Khan SI, Clark AM. Bioorg. Med. Chem. 2016; 24: 6119
    • 7b Marquise N, Chevallier F, Nassar E, Frederich M, Ledoux A, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Dorcet V, Mongin F. Tetrahedron 2016; 72: 825
    • 7c Phatchana R, Thongsri Y, Somwaeng R, Piboonpol K, Yenjai C. Phytochem. Lett. 2015; 13: 147
    • 7d Prachayasittikul S, Manam P, Chinworrungsee M, Isarankura-Na-Ayudhya C, Ruchirawat S, Prachayasittikul V. Molecules 2009; 14: 4414
    • 7e Mink K, Bracher F. Arch. Pharm. (Weinheim) 2007; 340: 429
    • 7f Lago JH. G, Chaves MH, Ayres MC. C, Agripino DG. Y, Maria CM. Planta Med. 2007; 73: 292
    • 7g Koyama J, Morita I, Kobayashi N, Osakai T, Usuki Y, Taniguchi M. Bioorg. Med. Chem. Lett. 2005; 15: 1079
  • 8 Rebstock A.-S, Mongin F, Trecourt F, Queguiner G. Tetrahedron 2004; 60: 2181
  • 9 Padwa A, Heidelbaugh TM, Kuethe JT. J. Org. Chem. 2000; 65: 2368
  • 10 Tong TH, Wong HN. C. Synth. Commun. 1992; 22: 1773
  • 11 Kraus GA, Kempema A. J. Nat. Prod. 2010; 73: 1967
  • 12 Taneichi Y, Shimada K, Korenaga T. Heterocycles 2018; 96: 440
    • 13a Sanchez LM, Sathicq AG, Romanelli GP, Gonzalez LM, Villa AL. Mol. Catal. 2017; 435: 1
    • 13b Jana A, Mondal J, Borah P, Mondal S, Bhaumik A, Zhao Y. Chem. Commun. 2015; 51: 10746
    • 13c Shen L, Cao S, Wu J, Zhang J, Li H, Liu N, Qian X. Green Chem. 2009; 11: 1414
  • 14 Alves T, De Oliveira AB, Snieckus V. Tetrahedron Lett. 1988; 29: 2135
  • 15 Chun YS, Lee JH, Kim JH, Ko YO, Lee S.-g. Org. Lett. 2011; 13: 6390
    • 16a Pan E, Cao S, Brodie PJ, Callmander MW, Randrianaivo R, Rakotonandrasana S, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Suh EM, Kingston DG. I. J. Nat. Prod. 2011; 74: 1169
    • 16b Palacios F, Herran E, Alonso C, Rubiales G, Lecea B, Ayerbe M, Cossio FP. J. Org. Chem. 2006; 71: 6020
  • 17 Hirai S, Horikawa Y, Asahara H, Nishiwaki N. Chem. Commun. 2017; 53: 2390
  • 18 Tadic D, Cassels BK, Cave A. Heterocycles 1988; 27: 407
  • 19 Pavel GV, Pavel KG, Tilichenko MN. Khim. Geterotsikl. Soedin. 1990; 950