Citation: Yan-Ming Shen, Lin-Lin Song, Xu-Hong Qian, You-Jun Yang. A scalable synthesis of 1-amino-5-cyanonaphthalene,a precursor for a nitric oxide probe(NO550)designed via the “dye assembly” principle[J]. Chinese Chemical Letters, ;2013, 24(01): 7-8. shu

A scalable synthesis of 1-amino-5-cyanonaphthalene,a precursor for a nitric oxide probe(NO550)designed via the “dye assembly” principle

1.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Xu-Hong Qian, You-Jun Yang,
Received Date: 3 December 2012
Available Online: 21 December 2012

A convenient and scalable synthesis of 1-amino-5-cyanonaphthalene was described.
- 1,5-Disubsituted naphthalene,
- Dye assembly,
- Fluorophore assembly,
- Fluorescent probe
1. [1]
  [1] T.Weil,T.Vosch,J.Hofkens,K.Peneva,K.Müllen,The rylene colorant family-tailored nanoemitters for photonics research and applications,Angew.Chem.Int. 49(2010)9068-9093.
2. [2]
  [2] W.Wang,S.V.D'Andrea,J.P.Freeman,J.Szmuszkovicz,Metal-halogen exchange reactions of 1,5-diiodonaphthalene.Synthesis of 1,5-disubstituted naphthalene derivatives,J.Org.Chem.56(1991)2914-2915.
3. [3]
  [3] M.Asakawa,P.R.Ashton,S.E.Boyd,et al.,Recognition of bipyridinium-based derivatives by hydroquinone- and/or dioxynaphthalene-based macrocyclic poly-ethers:from inclusion complexes to the self-assembly of[2] catenanes,J.Org. Chem.62(1997)26-37.
4. [4]
  [4] S.Kang,S.A.Vignon,H.R.Tseng,J.F.Stoddart,Molecular shuttles based on tetrathiafulvalene units and 1,5-dioxynaphthalene ring systems,Chem.Eur.J. 10(2004)2555-2564.
5. [5]
  [5] H.Bai,X.Wu,G.Shi,Synthesis and characterization of poly(1,5-naphthylene vinylene)and its copolymers with poly(2-methoxy-5-(20-ethylhexyloxy)-p-phe-nylene vinylene),Polymer 47(2006)1533-1537.
6. [6]
  [6] Y.W.Xu,G.S.Zhao,C.G.Shin,et al.,Caffeoyl naphthalenesul-fonamide derivatives as HIV integrase inhibitors,Bioorg.Med.Chem.11(2003)3589-3593.
7. [7]
  [7] R.P.Haugland,The handbook:A guide to fluorescent probes and labeling technologies,10th ed.,Invitrogen Corp.,Eugene,OR,2005.
8. [8]
  [8] Y.Zhang,X.Gao,K.Hardcastle,B.H.Wang,Water-soluble fluorescent boronic acid compounds for saccharide sensing:substituent effects on their fluorescence properties,Chem.Eur.J.12(2006)1377-1384.
9. [9]
  [9] Y.Yang,S.K.Seidlits,M.M.Adams,et al.,A highly selective low-background fluorescent imaging agent for nitric oxide,J.Am.Chem.Soc.132(2010) 13114-13116.
10. [10]
  [10] I.I.Schuster,1 3C NMR investigation of electronic interactions in 5-substituted 1-naphthonitriles,Magn.Reson.Chem.34(1996)301-310.
11. [11]
  [11] X.Gao,Y.Zhang,B.Wang,Naphthalene-based water-soluble fluorescent boronic acid isomers suitable for ratiometric and off-on sensing of saccharides at physio-logical pH,New J.Chem.29(2005)579-586.
12. [12]
  [12] K.W.Rosenmund,E.Struck,Das am ringkohlenstoff gebundene halogen und sein ersatz durch andere substituenten.I.mitteilung:ersatz des halogens durch die carboxylgruppe,Eur.J.Inorg.Chem.52(1919)1749-1756.
13. [13]
  [13] J.V.Braun,G.Manz,Fluoranthen und seine derivate.Ⅲ.mitteilung,Eur.J.Org. Chem.488(1931)111-126.
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沈阳化工大学材料科学与工程学院沈阳 110142