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Synthesis 2017; 49(10): 2231-2240
DOI: 10.1055/s-0036-1588712
DOI: 10.1055/s-0036-1588712
paper
Synthesis of 4-Nitro-N-phenyl-1,8-naphthalimide Annulated to Thia- and Azacrown Ether Moieties
Weitere Informationen
Publikationsverlauf
Received: 02. November 2016
Accepted after revision: 20. Januar 2017
Publikationsdatum:
14. Februar 2017 (online)
Abstract
Two convenient procedures for the synthesis of thia- and azacrown ether containing 4-nitro-1,8-naphthalimides have been developed. The first procedure is based on the amination of 1,8-naphthalic anhydride with crown-containing anilines. The second procedure includes the macrocyclization reaction of N-[1,2-bis(2-haloethoxy)phenyl]naphthalimide derivative with terminal thiols or methylamines. A strategy based on a macrocyclization is flexible and variable and also allows the use of the synthetic approach for more complex compounds.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588712.
- Supporting Information
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References
- 1 Chemical Sensors . Grundler P. Springer Verlag; Berlin: 2007
- 2 Desvergne JP, Czarnik AW. NATO ASI Series 1997; 492
- 3 Panchenko PA, Fedorova OA, Fedorov YuV. Russ. Chem. Rev. 2014; 83: 155
- 4a Demeter A, Burces T, Biczуk L. J. Phys. Chem. 1996; 100: 2001
- 4b Cao H, Chang V, Hernandez R, Heagy MD. J. Org. Chem. 2005; 70: 4929
- 4c Esteban-Gómez D, Fabbrizzi L, Licchelli M. J. Org. Chem. 2005; 70: 5717
- 5 He H, Mortellaro MA, Leiner MJ. P, Young ST, Fraatz RJ, Tusa JK. Anal. Chem. 2003; 75: 549
- 6 Nandhikonda P, Begaye MP, Heagy MD. Tetrahedron Lett. 2009; 50: 2459
- 7 Chen T, Zhu W, Xu Y, Zhang S, Zhang X, Qian X. Dalton Trans. 2010; 39: 1316
- 8 Bricks JL, Kovalchuk A, Trieflinger C, Nofz M, Büschel M, Tolmachev AI, Daub J, Rurack K. J. Am. Chem. Soc. 2005; 127: 13522
- 9 Rurack K, Resch-Genger U, Bricks JL, Spieles M. Chem. Commun. 2000; 2103
- 10 Cosnard F, Wintgens V. Tetrahedron Lett. 1998; 39: 2751
- 11 Panchenko PA, Fedorov YuV, Fedorova OA, Izmailov BA, Vasnev VA, Istratov VV, Makeeva EA, Rumyantseva MN, Gaskov AM. Mendeleev Commun. 2011; 21: 12
- 12 Sergeeva AN, Panchenko PA, Fedorov YuV, Fedorova OA. Protect. Met. Phys. Chem. Surf. 2012; 48: 524
- 13a Panchenko PA, Fedorov YV, Fedorova OA, Jonusauskas G. Dyes Pigm. 2013; 98: 347
- 13b Selector SL, Bogdanova LB, Shokurov AV, Panchenko PA, Fedorova OA, Arslanov VV. Macroheterocycles 2014; 7: 311
- 14a Fedorova O, Fedorov Y, Oshchepkov M. J. Electroanalysis 2012; 8: 1739
- 14b Fedorova O, Fedorov Y, Oshchepkov M, Dobrovolskaya M. J. Phys. Org. Chem. 2012; 25: 835
- 15a Alfimov MV, Gromov SP, Fedorov YuV, Fedorova OA, Vedernikov AI, Churakov AV, Kuz’mina LG, Howard JA. K, Bossmann S, Braun A, Woerner M, Sears DF, Saltiel J. J. Am. Chem. Soc. 1999; 121: 4992
- 15b Fedorova OA, Fedorov YV, Vedernikov AI, Gromov SP, Yescheulova OV, Alfimov MV, Woerner M, Bossmann S, Braun A, Saltiel J. J. Phys. Chem. A. 2002; 106: 6213
- 16a Panchenko PA, Fedorov YuV, Fedorova OA, Perevalov VP, Jonusauskas G. Russ. Chem. Bull. 2009; 58: 1233
- 16b de Silva AP, Gunaratne HQ. N, Gunnlaugsson T, Huxley AJ. M, McCoy CP, Rademacher JT, Rice TE. Chem. Rev. 1997; 97: 1515
- 16c de Silva AP, Moody TS, Wright GD. Analyst 2009; 134: 2385
- 17a Panchenko PA, Fedorov YuV, Perevalov VP, Jonusauskas G, Fedorova OA. J. Phys. Chem. A. 2010; 114: 4118
- 17b Parkesh R, Lee TC, Gunnlaugsson T. Org. Biomol. Chem. 2007; 5: 310
- 18 Oshchepkov MS, Perevalov VP, Kuz’mina LG, Anisimov AV, Fedorova ОA. Russ. Chem. Bull. 2011; 3: 468
- 19a Fedorova ОA, Vedernikov АI, Yescheulova OV, Tsapenko PV, Pershina YV, Gromov SP. Russ. Chem. Bull. 2000; 49: 1853
- 19b Fedorova OA, Vedernikov AI, Yescheulova OV, Pershina YV, Tsapenko PV, Gromov SP. Synth. Commun. 2002; 32: 1909
- 20a Dix JP, Vogtle F. Chem. Ber. 1980; 113: 457
- 20b Vogel’s Textbook of Practical Organic Chemistry . Vogel AI, Furniss BS, Hannaford AJ, Smith PW. G, Tatchell AR. Wiley; New York: 1989
- 21 Nakaya K, Funabiki K, Muramatsu H, Shibata K, Matsui M. Dyes Pigm. 1999; 43: 235
- 22 Abramov AA, Averina NV, Iofa BZ, Samoshin VV, Ivanova NA, Sapozhnlkov YuA, Zefirov NS. Chem. Heterocycl. Comp. 1997; 33: 982
- 23a Bandaranayake WM, Begley MJ, Brown BO, Clarke DG, Crombie L, Whiting DA. J. Chem. Soc., Perkin Trans. 1 1974; 998
- 23b Sartori G, Casiraghi G, Bolzoni L, Casnati G. J. Org. Chem. 1979; 44: 803
- 24 Portnyagin IA, Lunin VV, Nechaev MS. Russ. Chem. Bull. Int. Ed. 2007; 56: 926
- 25 Yam VW.-W, Pui Y.-L, Li W.-P, Lo KK.-W, Cheung K.-K. J. Chem. Soc., Dalton Trans. 1998; 3615