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Synthesis 2014; 46(12): 1659-1666
DOI: 10.1055/s-0033-1341063
DOI: 10.1055/s-0033-1341063
paper
Synthesis of Naphthopyrans and Spironaphthoxazines Annulated to Crown Ether Fragments through a Macrocyclization Strategy
Further Information
Publication History
Received: 23 January 2014
Accepted after revision: 06 March 2014
Publication Date:
27 March 2014 (online)
Abstract
A practical and convenient procedure for the synthesis of naphthopyrans and spironaphthoxazines annulated to crown ether fragments has been developed. This innovative and general strategy based on a macrocyclization is a flexible and variable synthetic approach for other similar types of compounds.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Organic Photochromic and Thermochromic Compounds . Vol. 1. Crano JC, Guglielmetti RJ. Plenum Press; New York: 1999: 400
- 1b Organic Photochromic and Thermochromic Compounds . Vol. 2. Crano JC, Guglielmetti RJ. Plenum Press; New York: 1999: 473
- 2 Photochromism: Molecules and Systems . Dürr H, Bouas-Laurent H. Elsevier; Amsterdam: 2003: 1044
- 3 Minkin V. Chem. Rev. 2004; 104: 2751
- 4 Lokshin V, Samat A, Metelitsa AV. Russ. Chem. Rev. 2002; 71: 893
- 5 Hepworth JD, Heron BM In Photochromic Naphthopyrans in Functional Dyes . Kim S.-H. Elsevier; Amsterdam: 2006. 271
- 6a Hamada F, Ito R. Macromol. Rapid Commun. 1994; 15: 531
- 6b Hamada F, Hoshi K, Higuchi Y, Murai K, Akagami Y, Ueno A. J. Chem. Soc., Perkin Trans. 2 1996; 2567
- 7 Fedorova OA, Ushakov EN, Fedorov YV, Strokach YP, Gromov SP. Macrocyclic Chemistry: Current Trends and Future Perspectives . Gloe K. Springer; Berlin: 2005: 235
- 8 Alfimov MV, Fedorova OA, Gromov SP. J. Photochem. Photobiol., A. 2003; 158: 183
- 9 Paramonov SV, Lokshin V, Fedorova OA. J. Photochem. Photobiol., C 2011; 12: 209
- 10a Pieroni O, Ciardelli F. Trends Polym. Sci. 1995; 3: 282
- 10b Matsushima R, Nishiyama M, Doi M. J. Photochem. Photobiol., A. 2001; 139: 63
- 11a Inouye M, Kim K, Kitao T. J. Am. Chem. Soc. 1992; 114: 778
- 11b Takase M, Inouye M. Chem. Commun. 2001; 2432
- 12a Jukes RT. F, Bozic B, Hartl F, Belser P, De Cola L. Inorg. Chem. 2006; 45: 8326
- 12b Belser P, De Cola L, Hartl F, Adamo V, Bozic B, Chriqui Y, Iyer VM, Jukes RT. F, Kuhni J, Querol M, Roma S, Salluce N. Adv. Funct. Mater. 2006; 16: 195
- 12c Wu H, Zhang D, Su L, Ohkubo K, Zhang C, Yin S, Mao L, Shuai Z, Fukuzumi S, Zhu D. J. Am. Chem. Soc. 2007; 129: 6839
- 13a Fedorova OA, Maurel F, Chebun’kova AV, Strokach YuP, Valova TM, Kuzmina LG, Howard JA. K, Wenzel M, Gloe K, Lokshin V, Samat A. J. Phys. Org. Chem. 2007; 20: 469
- 13b Chebun’kova AV, Gromov SP, Strokach YP, Valova TM, Alfimov MV, Fedorova OA, Lokshin V, Samat A. Mol. Cryst. Liq. Cryst. 2005; 430: 67
- 13c Fedorova OA, Strokach YuP, Chebun’kova AV, Valova TM, Gromov SP, Alfimov MV, Lokshin V, Samat A. Russ. Chem. Bull. 2006; 55: 287
- 13d Ahmed SA, Tanaka M, Ando H, Iwamoto H, Kimura K. Eur. J. Org. Chem. 2003; 2437
- 13e Ahmed SA, Tanaka M, Ando H, Iwamoto H, Kimura K. Tetrahedron 2004; 60: 3211
- 13f Ushakov EN, Nazarov VB, Fedorova OA, Gromov SP, Chebun’kova AV, Alfimov MV, Barigellew F. J. Phys. Org. Chem. 2003; 16: 306
- 13g Fedorova OA, Maurel F, Ushakov EN, Nazarov VB, Gromov SP, Chebunkova AV, Feofanov AV, Alaverdian IS, Alfimov MV, Barigellew F. New J. Chem. 2003; 27: 1720
- 13h Nazarov VB, Fedorova OA, Brichkin SB, Nikolaeva TM, Gromov SP, Chebun’kova AV, Alfimov MV. Russ. Chem. Bull. 2003; 52: 2661
- 13i Kumar S, Hernandez D, Hoa B, Lee Y, Yang YS, McCurdy A. Org. Lett. 2008; 10: 3761
- 13j Wada F, Arata R, Goto T, Kikukawa K, Matsuda T. Bull. Chem. Soc. Jpn. 1980; 53: 2061
- 14a Yagai S, Kitamura A. Chem. Soc. Rev. 2008; 37: 1520
- 14b Kume S, Nishihara H In Photofunctional Transition Metal Complexes, Series Structure and Bonding . Vol. 123. Yam VW. W. Springer; Berlin: 2007: 79
- 14c Joachim C, Gimzewski JK, Aviram A. Nature 2000; 408: 541
- 15 Paramonov SV, Lokshin V, Smolentsev AB, Glebov EM, Korolev V, Basok SS, Lysenko KA, Delbaere S, Fedorova OA. Tetrahedron 2012; 68: 7873
- 16 Desvergne J.-P, Lahrahar N, Gotta M, Zimmermann Y, Bouas-Laurent H. J. Mater. Chem. 2005; 15: 2873
- 17 Brunet E, Alonso MT, Juanes O, Velasco O, Rodriguez-Ubis C. Tetrahedron 2001; 57: 3105
- 18 Delorme D, Ducharme Y, Brideau C, Chan CC, Chauret N, Desmarais S, Dube D, Falgueyret JP, Fortin R, Guay J, Hamel P, Jones TR, Lepine C, Li C, McAuliffe M, McFarlane CS, Nicoll-Griffith DA, Riendeau D, Yergey JA, Girard Y. J. Med. Chem. 1996; 39: 3951
- 19 Gabbutt CD, Hepworth JD, Heron BM, Rahman MM. J. Chem. Soc., Perkin Trans. 1 1994; 1733
- 20 CCDC-982086 contains the supplementary crystallographic data of 7b for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk.
- 21 Bogaschenko T, Basok S, Kulygina C, Lyapunov A, Lukyanenko N. Synthesis 2002; 2266
- 22 Fedorova OA, Vedernikov AI, Yescheulova OV, Tsapenko PV, Pershina YV, Gromov SP. Russ. Chem. Bull. 2000; 49: 1853