Simultaneous displacement of a nitro group during coupling of diazotized o-nitroaniline with phenols

• Authors: Renata Farkas , Mercedesz Törincsi , Pal Kolonits , Jenö Fekete , Oscar Alonso , Lajos Novak
• Languages of publication: EN

Abstracts

EN

During the diazo-coupling reaction, nucleophilic displacement of a nitro group was also observed. This was the main reaction (1→7) when the starting amine bore either a chlorine or methoxy group at the para position (1b–c). The newly prepared compounds (7) might serve as convenient building blocks in synthesis of some heterocycles. [...]

Keywords

EN

Azo-coupling; Nitro group; Replacement reaction; Diazene derivatives; Benzotriazoles

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 2
• Pages: 300-307

Dates

published

1 - 4 - 2010

online

23 - 3 - 2010

Contributors

author

Renata Farkas

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Research Group for Alkaloid Chemistry, 1111, Budapest, Hungary

author

Mercedesz Törincsi

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Research Group for Alkaloid Chemistry, 1111, Budapest, Hungary

author

Pal Kolonits

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Research Group for Alkaloid Chemistry, 1111, Budapest, Hungary

author

Jenö Fekete

• Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, 1111, Budapest, Hungary

author

Oscar Alonso

• ISDIN, 08006, Barcelona, Spain

author

Lajos Novak

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Research Group for Alkaloid Chemistry, 1111, Budapest, Hungary

References

• [1] J. March, Advanced Organic Chemistry, 4th edition (John Wiley & Sons, New York, 1992) 503, 635, 1079
• [2] K.H. Saunders, R.L.M. Allen, Aromatic Diazo Compounds, 3rd edition (E. Arnold Ltd., London, 1985)
• [3] A.F. Hegarty, In: S. Patai (Ed.), The Chemistry of Diazonium and Diaza groups, Part 2, (John Wiley & Sons, New York, 1978) 545
• [4] I. Szele, H. Zollinger, Topics in Current Chemistry 112, 1 (1983); J.R. Penton, Helv. Chim. Acta 65, 122 (1983); D. Bahulayan, L. John, M. Lalithambika, Synth. Commun. 33, 863 (2003); H.A. Dabbagh, A.Teimouri, A.N. Chermahini, Dyes and Pigments 73, 239 (2007); and references cited therein
• [5] A.R. Katritzky, S. Rachwal, G.J. Hitchings, Tetrahedron 47, 2683 (1991) http://dx.doi.org/10.1016/S0040-4020(01)87080-0[Crossref]
• [6] A.R. Katritzky, X. Lan, J. Z. Yang, O. Denisko, Chem. Rev. 98, 409 (1998) http://dx.doi.org/10.1021/cr941170v[Crossref]
• [7] A.R. Katritzky, Heterocycl. Chem. 36, 1501 (1999) http://dx.doi.org/10.1002/jhet.5570360611[Crossref]
• [8] S.J. Li, A. Gutta, O. Vogl, Monatsh. Chem. 114, 93 (1983) http://dx.doi.org/10.1007/BF00799954[Crossref]
• [9] S.J. Li, A. C. Albertsson, W. Bassett, O. Vogl, Monatsh. Chem. 115, 853 (1984) http://dx.doi.org/10.1007/BF01120980[Crossref]
• [10] S. Li, W. Bassett Jr, F. Xi, O. Vogl, Acta Polimerica 36, 81 (1985) http://dx.doi.org/10.1002/actp.1985.010360205[Crossref]
• [11] A.G. Koutsimpelis, C.G. Screttas, O. Igglessi-Markopoulou, Heterocycles 65, 1393 (2005) http://dx.doi.org/10.3987/COM-04-10304[Crossref]
• [12] F. He, X. Liu, B. Wang, Z. Li, J. Chem. Res. 809 (2006) [Crossref]
• [13] G. Scapin et al., Biochemistry 42, 11451 (2003) http://dx.doi.org/10.1021/bi035098j[Crossref]
• [14] P.G. Baraldi et al., Arzneimittel-Forschung 52, 273 (2002)
• [15] F. Al-Omran, R.M. Mohareb, M. Rafat, A.A. El-Khair, J. Heterocycl. Chem. 39, 877 (2002) http://dx.doi.org/10.1002/jhet.5570390504[Crossref]
• [16] C. Trullas, C. Pelejero, J. Corbera Arjona, O. Jimenez Alonso, L. Novak, Spain Pat. Appl. (2008), ES 2300199 A1 20080601
• [17] K. Golz-Berner, L. Zastrow, S. Miton, Ger. Pat. Appl. (2008), DE 102007010861 A1 20080904
• [18] E. Woldt, S. Schmidt, U.S. Pat. Appl. (2006), US 2006084754 A1 20060420
• [19] A. Goeppel, Eur. Pat. Appl. (2003), EP 1308153 A2 20030507
• [20] K. Venkataraman, The Chemistry of Synthetic Dyes (Academic Press, New York, 1970)
• [21] A.N. Pankratov, Helv. Chim. Acta 87, 1561 (2004) http://dx.doi.org/10.1002/hlca.200490143[Crossref]
• [22] U. Pindur, H. Witzel, Deutsche Apotheker Zeitung 128, 2127 (1988)
• [23] J.F. Bunnett, R.E. Zahler, Chem. Rev. 49, 273 (1951), and references cited therein http://dx.doi.org/10.1021/cr60153a002[Crossref]
• [24] B. Bolto, J. Miller, Austr. J. Chem. 9, 74 (1956)
• [25] W.M. Cummings, K.L. Krenz, J. Org. Chem. 37,3929 (1972) http://dx.doi.org/10.1021/jo00797a035[Crossref]
• [26] I.A. Khalfina, V.M. Vlasov, Russian J. Org. Chem. 33, 665 (1997)
• [27] M. Massacret, P. Lhoste, R. Lakhmiri, T. Parella, D. Sinou, Eur. J. Org. Chem. 10, 2665 (1999) http://dx.doi.org/10.1002/(SICI)1099-0690(199910)1999:10<2665::AID-EJOC2665>3.0.CO;2-0[Crossref]
• [28] M. Rahimizade, M. Pordel, M. Bakavoli, H. Eshghi, A. Shiri, Mendeleev Commun. 19, 161 (2009) http://dx.doi.org/10.1016/j.mencom.2009.05.017[Crossref]
• [29] Z.J. Allen, J. Podstata, Collect. Czech. Chem. Commun. 29, 2264 (1964) [Crossref]
• [30] J. Allen, Aromatic Diazo Compounds (E. Arnold, London, 1985)
• [31] I.L. Dalinger, T.I. Cherkasova, S.A. Shevelev, Mendeleev Commun. 2, 58 (1997) http://dx.doi.org/10.1070/MC1997v007n02ABEH000670[Crossref]
• [32] A.G. Kautsimpelis, G. Ganstantinis, O. Iglessi-Markopoulou, Heterocycles 65, 1393 (2005). http://dx.doi.org/10.3987/COM-04-10304[Crossref]
• [33] M. Pizzotti, M. Ragaini, S. Cenini, Gazz. Chim. Ital. 123, 683 (1993)
• [34] S. Schnatterer, F. Lochaas, W. Knauf, K. Seeger, US Pat. Appl. US 2008293824 A1 20081127
• [35] J. Belusa, M. Krchuak, E. Polacek, E. Rabusic, Chem. Zvesti, 26, 53 (1972)
• [36] C.O. Gorchs, A.J.O. Jimenez, C.C.R. Trullas, A.J. Corbera, C.D. Panyella, L. Novak, Int. Pat. Appl. WO 2008131921 A1 20081106
• [37] O. Taketoshi, Y. Ryoko, Ch. Shigegaki, O. Shigeru, N. Atsuro, Bioorg. Med. Chem., 433 (2004)
• [38] N.N. Vorozhtsov, A.T. Troshenko, Zh.l Obshck Khim. 8, 431 (1938)

Identifiers

DOI

10.2478/s11532-009-0150-8