Synthesis and Photoreaction of 2-Amino-3-cyano-4-aryl-4H-pyrans

Wuji Sun; Yangye Jiang; Hong Yan; Xiuqing Song

doi:10.1071/CH14113

RESEARCH ARTICLE

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Synthesis and Photoreaction of 2-Amino-3-cyano-4-aryl-4H-pyrans

Wuji Sun ^A , Yangye Jiang ^A , Hong Yan ^A ^B and Xiuqing Song ^A

+ Author Affiliations

- Author Affiliations

^A College of Life Science and Bioengineering, Beijing University of Technology, Pingleyuan Street No. 100, Chaoyang District, Beijing 100124, China.

^B Corresponding author. Email: hongyan@bjut.edu.cn

Australian Journal of Chemistry 68(2) 273-281 https://doi.org/10.1071/CH14113
Submitted: 3 March 2014 Accepted: 25 April 2014 Published: 4 June 2014

Abstract

A series of 2-amino-3-cyano-4-aryl-4H-pyrans (1) were synthesised by reacting malononitrile, ethyl acetoacetate, and aromatic aldehydes under ultrasound irradiation. The photochemical properties, including the photostability and photoreaction of 1, were investigated in conventional solvents. The results indicated that compounds 1 were unstable and underwent a photoreaction to the 1,3-butadienes under irradiation with UV light. A mechanism for the photoreaction is proposed and investigated using electron spin resonance spectroscopic techniques. The 1,3-butadiene structures were determined by ¹H and ¹³C NMR spectra, high-resolution mass spectrometry, and single crystal X-ray diffraction analysis.

References

[1] (a) P. W. Smith, S. L. Sollis, P. D. Howes, P. C. Cherry, I. D. Starkey, K. N. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, J. Med. Chem. 1998, 41, 787.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhtF2murg%3D&md5=0fd35261ea7d9bc7e9b816647ae9c321CAS | 9526555PubMed |
      (b) J. Marco-Contelles, R. León, E. Morales, M. Villarroya, A. G. García, Tetrahedron Lett. 2004, 45, 5203.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Akbari, Z. Azami-Sardooei, A. Hosseini-Nia, J. Korean Chem. Soc. 2013, 57, 455.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. R. Saundane, K. Vijaykumar, A. V. Vaijinath, Bioorg. Med. Chem. Lett. 2013, 23, 1978.
         | Crossref | GoogleScholarGoogle Scholar |

[2] (a) A. Adbel-Fattah, Liebigs Ann. Chem. 1998, 585.
(b) C. O’Callaghan, T. McMurry, J. Chem. Res. Synop. 1995, 6, 214.
(c) S. Srivastava, S. Batra, A. Bhaduri, Indian J. Chem. B 1996, 35, 602.

[3] N. S. Ibrahim, Heterocycles 1986, 24, 935.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XmtVyksLw%3D&md5=5e6807b02946c46108b4d1bdb350030eCAS |

[5] (a) X. Zhu, W. Li, H. Yan, R. Zhong, J. Photochem. Photobiol. Chem. 2012, 241, 13.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XpsVyjs70%3D&md5=2b85fed699ba5cb56f569271d4de2e29CAS |
      (b) H. Xin, W. Sun, H. Yan, X. Song, J. Photochem. Photobiol. Chem. 2013, 267, 49.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) X. Zhu, C. Ni, H. Yan, R. Zhong, J. Photopolym. Sci. Technol. 2009, 22, 379.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) X. N. C. S. X. Zhu, H. Yan, R. Zhong, Chin. J. Org. Chem 2010, 30, 276.

[6] M. H. Elnagdi, R. M. Abdel-Motaleb, M. Mustafa, M. F. Zayed, E. M. Kamel, J. Heterocycl. Chem. 1987, 24, 1677.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXlsV2nt7Y%3D&md5=b1aa1d8da48e46c54b74bc79af1a74bfCAS |

[7] (a) I. Saito, H. Takami, T. Matsuura, Tetrahedron Lett. 1975, 16, 3155.
| Crossref | GoogleScholarGoogle Scholar |
(b) O. Chapman, P. Cleveland, E. Hoganson, Chem. Commun. 1966, 101.

[8] D. Armesto, A. Albert, F. H. Cano, N. Martín, A. Ramos, M. Rodriguez, J. L. Segura, C. Seoane, J. Chem. Soc., Perkin Trans. 1 1997, 3401.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXns1Cisrw%3D&md5=062de95f80b3ace0c4004144bae72b2fCAS |

[9] (a) W. Teshima, Y. Nomura, N. Tanaka, H. Urabe, M. Okazaki, Y. Nahara, Biomaterials 2003, 24, 2097.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhslGqtLg%3D&md5=a085ce8ca9fe38a99ce8c9fc4384764bCAS | 12628830PubMed |
      (b) Y. Li, Q. Wang, J. Guo, G. Wu, Mater. Sci. Eng. C 1999, 10, 25.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Allouch, V. Roubaud, R. Lauricella, J.-C. Bouteiller, B. Tuccio, Org. Biomol. Chem. 2003, 1, 593.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) C. Frejaville, H. Karoui, B. Tuccio, F. L. Moigne, M. Culcasi, S. Pietri, R. Lauricella, P. Tordo, J. Med. Chem. 1995, 38, 258.
         | Crossref | GoogleScholarGoogle Scholar |

[10] D. Kumar, V. B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 2009, 44, 3805.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXoslGhsb8%3D&md5=62a1e638a5cd4d39ad16858dd15bf3bfCAS | 19419801PubMed |

[11] P. Bhattacharyya, K. Pradhan, S. Paul, A. R. Das, Tetrahedron Lett. 2012, 53, 4687.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVOqur%2FM&md5=67487c56cea50c9ae6157931f530ed8aCAS |

[12] X.-S. Wang, Z.-S. Zeng, M.-M. Zhang, Y.-L. Li, D.-Q. Shi, S.-J. Tu, X.-Y. Wei, Z.-M. Zong, J. Chem. Res. 2006, 2006, 228.
| Crossref | GoogleScholarGoogle Scholar |

[13] G. P. Lu, C. Cai, J. Heterocycl. Chem. 2011, 48, 124.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjslGrtrY%3D&md5=fa064db33367631a87c6d9e409b9f877CAS |

[14] G. Sheldrick, ABSCOR program 1996 (University of Göttingen: Göttingen).

[15] G. Sheldrick, SHELXS-97 program 1997 (University of Göttingen: Göttingen).

[16] G. Sheldrick, SHELXL-97 program 1997 (University of Göttingen: Göttingen).

Synthesis and Photoreaction of 2-Amino-3-cyano-4-aryl-4H-pyrans

Abstract

References

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