Abstract
6-(Substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones were prepared from β-aryl glutaconic acid, which, on fusion with aniline, results in 4-(4-ethoxyphenyl)-1-phenylpyridine-2,6(1H,5H)-dione. This, on further treatment with phosphorus oxychloride gave 6-chloro-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinone, and further treatment with secondary amines yielded 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones. These were subjected to azo coupling with different aryldiazonium chlorides furnishing two isomers, which were separated by column chromatography. All compounds were characterized by elemental analysis, and use of IR and NMR spectral data, and were evaluated for antimicrobial activity.
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Dorigo P, Gaion RM, Belluco P, Fraccarollo D, Maragno I, Bobieri G, Benetollo F, Mosti L, Orsini F (1993) J Med Chem 36:2475
Farah AE, Alousi AA (1978) Life Sci 22:1139
Alousi AA, Canter JM, Monterano MJ, Fort DJ, Ferrari RA (1983) J Cardiovasc Pharmacol 5:792
Paulvannan K, Chen T (2000) J Org Chem 65:6160
Rodgers JD, Wang H, Patel M, Arvanitis A, Cocuzza AJ (2005) US Patent 6,969,721 B2. Bristol-Myers Squibb Pharma. Princeton
Flynn DL, Petillo PA (2007) US Patent 7,202,257 B2. Deciphera Pharma, LLC. Lawrence
Pemberton N (2007) Synthesis and functionalization of ring fused 2-pyridones - targeting pilli formation in E. Coli. Akademik avhandling. Department of Chemistry, Umea University, Sweden
Prakash HS, Senthilkumar SP (2004) Curr Org Chem 8:1521
Misic-Vukovic M, Radojkovic-Velickovic M (1998) J Serb Chem Soc 63:585
Uscumlic G, Mijin D, Valentic N, Vajs V, Susic B (2004) Chem Phys Lett 397:148
Forlani L, Gristoni G, Boga C, Todesco PE, Del Vechio E, Salva S, Monari M (2002) Arkivoc 11:198
Kirk-Othmer (1968) Encyclopedia of chemical technology, 2nd rev edn. Wiley Interscience Publication, Wiley
Armarego WLF (1977) In: Taylor EC, Weisberger A (eds) Stereochemistry of heterocyclic compounds. Wiley, New York
Martin WB, Martell AE (1948) J Am Chem Soc 70:1817
Patel NB, Patel AK (2004) Indian J Chem 45B:1774
Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Kokai 77, 77,066. Yamanouchi Pharmaceutical Co. Ltd., Japan
Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Chem Abstr 87:201328h
Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Yakuguku Zasshi 99:558
Silverstein RM, Webster FX (1998) Spectrometric identification of organic compounds, vol 6. Wiley, New York
Dyer JR, Cazes J, Marcel D, Khadatare AM, Jitkar SC, Malcolm R, Thomas N, Febiger L (1987) Application of absorption spectroscopy of organic compounds, vol 6. Lea & Febiger, Philadelphia
Matoba K, Fukushima A, Arai H, Yamazaki T (1979) Chem Bull 27:242
Edward DI (1980) Antimicrobial drug action, vol 1. Macmillan Press, London and Basingstoke, p 8
Barry AL (1976) The antimicrobial susceptibility test, principle and practices. Lea & Febiger, Philadelphia
Acknowledgments
The authors are grateful to the Head of the Chemistry Department, Veer Narmad South Gujarat University, Surat, Gujarat, for providing laboratory facilities, and to the SAIF, Punjab University, Chandigarh, for NMR spectra.
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Patel, N.B., Gandhi, A.I. & Sharma, R.D. Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones via azo coupling. Monatsh Chem 141, 1123–1133 (2010). https://doi.org/10.1007/s00706-010-0366-5
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DOI: https://doi.org/10.1007/s00706-010-0366-5