A Novel Ring Transformation of Nitrobenzocrown Ethers as a Route to Nitrobenzoazacrown Compounds

Abstract

A method for the synthesis of previously unknown nitro derivatives of benzoazacrown compounds in which nitrogen is conjugated with the benzene ring, based on readily available benzocrown ethers used as synthons, has been developed. This approach can serve as a useful tool in the synthesis of diverse benzoazacrown derivatives.

Key words

ring opening - crown compounds - podands - ring closure - nitrobenzoazacrown compounds

References

• 1a Cation Binding by Macrocycles   Inoue Y. Gokel GW. Marcel Dekker; New York: 1990. 
• 1b Izatt RM. Pawlak K. Bradshaw JS. Bruening RL. Chem. Rev.  1991,  91:  1721 
• 2a de Silva AP. Gunaratne HQN. Gunnlaugsson T. Huxley AJM. McCoy CP. Rademacher JT. Rice TE. Chem. Rev.  1997,  97:  1515 
• 2b Alfimov MV. Gromov SP. In Applied Fluorescence in Chemistry, Biology, and Medicine   Rettig W. Strehmel B. Schrader S. Seifert H. Springer Verlag; Berlin: 1999.  p.161 
• 2c Valeur B. Leray I. Coord. Chem. Rev.  2000,  205:  3 
• 2d Shinkai S. In Comprehensive Supramolecular Chemistry   Vol. 1:  Gokel GW. Pergamon; Oxford: 1996.  p.671 
• 2e Gromov SP. Alfimov MV. Russ. Chem. Bull.; 1997, 46: 611. Izv. Akad. Nauk, Ser. Khim.  1997,  641 
• 2f Mishra A. Behera RK. Behera PK. Mishra BK. Behera GB. Chem. Rev.  2000,  100:  1973 
• 3a Yordanov AT. Roundhill DM. Coord. Chem. Rev.  1998,  170:  93 
• 3b Gloe K. Graubaum H. Wüst M. Rambusch T. Seichter W. Coord. Chem. Rev.  2001,  222:  103 
• 4 Bühlmann P. Pretsch E. Bakker E. Chem. Rev.  1998,  98:  1593 
• 5 Feiters MC. In Comprehensive Supramolecular Chemistry   Vol. 10:  Reinhoudt DN. Pergamon; Oxford: 1996.  p.267 
• 6a Bradshaw JS. Krakowiak KE. Izatt RM. Aza-Crown Macrocycles   Wiley; New York: 1993. 
• 6b Krakowiak KE. Bradshaw JS. Zamecka-Krakowiak DJ. Chem. Rev.  1989,  89:  929 
• 7a Lockhart JC. Robson AC. Thompson ME. Furtado SD. Kaura CK. Allan AR. J. Chem. Soc., Perkin Trans. 1  1973,  577 
• 7b Pedersen CJ, and Bromels MH. inventors; US Patent  3847949.  ; Chem. Abstr. 1975, 82, 73049
• 7c Högberg SAG. Cram DJ. J. Org. Chem.  1975,  40:  151 
• 7d Lockhart JC. Thompson ME. J. Chem. Soc., Perkin Trans. 1  1977,  202 
• 8a Kost AN. Gromov SP. Sagitullin RS. Tetrahedron  1981,  37:  3423 
• 8b Gromov SP. Kost AN. Heterocycles  1994,  38:  1127 
• 8c Gromov SP. Heterocycles  2000,  53:  1607 
• 9a Ivanov EI. Terent’ev PB. Polischuk AA. Zakharov KS. Subbotin BS. Khim. Geterotsikl. Soedin.  1985,  1573 ; Chem. Abstr. 1987, 106, 4591y
• 9b Töke L. Bitter I. Agai B. Hell Z. Lindner E. Toth K. Horvath MA. Szöllosy A. Harfouch S. Pungor E. Liebigs Ann. Chem.  1988,  761 
• 10a Gromov SP. Vedernikov AI. Dmitrieva SN. Russ. Chem. Bull.; 1999, 48: 1190. Izv. Akad. Nauk, Ser. Khim.  1999,  1204 
• 10b Gromov SP, Vedernikov AI, and Dmitrieva SN. inventors; RF Patent  2161153.  ; Chem. Abstr. 2002, 136, 401792
• 11a Pacey GE. Wu YP. Bubnis BP. Synth. Commun.  1981,  11:  323 
• 11b Ungaro R. El Haj B. Smid J. J. Am. Chem. Soc.  1976,  98:  5198