Synthesis of 1,8-naphthyridine-4(1H)-one sulfonamides by thermolysis of 2-aminopyridinemethylene (Meldrum's acid) derivative

Synthetic Communications

Volumn 38, Issue 1, 2008, Pages 15-20

  Da Silva, Luiz Everson ^a   Joussef, Antonio Carlos ^b   Nunes, Ricardo José ^b   De Oliveira, Kely Navakoski ^b  

^a FEDERAL UNIVERSITY OF MATO GROSSO   (Brazil)

^b SANTA CATARINA STATE UNIVERSITY   (Brazil)

Author keywords

Meldrum's acid; Naphthyridines; Sulfonamides

Indexed keywords

1,8 NAPHTHYRIDINE DERIVATIVE; 2 AMINOPYRIDINE DERIVATIVE; 5,7 DIMETHYL 4 OXO N (2 PHENYLETHYL) 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 SULFONAMIDE; 5,7 DIMETHYL 4 OXO N PHENYL 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 SULFONAMIDE; ANTIVIRUS AGENT; N BENZYL 5,7 DIMETHYL 4 OXO 1,4 DIHYDRO [1,8]NAPHTHYRIDINE 3 SULFONAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 37549004800     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701648744     Document Type: Article

References (13)

1. Chan, L.; Jin, H.; Stefanac, T.; Lavellée, J.-F.;Falardeau, G.; Wang, W.; Bédard, J.; May, S.; Yuen, L. Discovery of 1,6-naphthyriridines as a novel class of potent and seletive human cytomegalovirus inhibitors. J. Med. Chem. 1999, 42, 3023-3025.
2. Chan, L.; Stefanac, T.; Turcotte, N.; Hu, Z.; Chen, Y.; Bédard, J.; May, S.; Jin, H. Design and evaluation of dihydroisoquinolines as potent and orally bioavailable human cytomegalovirus inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 1477-1480.
3. Falardeau, G.; Chan, L.; Stefanac, T.; May, S.; Jin, H.; Lavalée, J.-F. Bioorg. Med. Chem. Lett. 2000, 11, 2769-2770.
4. Graf, G. I.; Hastreiter, D.; Silva, L. E.; Rebelo, R. A.; Montalban, A. G.; McKillop, A. The synthesis of aromatic diazatricycles from phenylenediamine-bis( methylene Meldrum's acid) derivatives. Tetrahedron 2002, 58, 9095-9100.
5. Bedard, J.; May, S.; L, Heureux, L.; Stamminger, T.; Copsey, A.; Drach, J.; Huffman, J.; Chan, L.; Jin, H.; Rando, R. F. Antiviral properties of a series of 1,6-naphthyridine and 7,8-dihydroisoquinoline derivatives exhibiting potent activity against human cytomegalovirus. Antimicrobial Agents and Chemotherapy 2000, 44 (4), 929-937.
6. Chan, L.; Stefanac, T.; Lavellée, J.-F.;Jin, H.; Bédard, J.; May, S.; Falardeau, G. Design and synthesis of new potent human cytomegalovirus (HCMV) inhibitors based on internally hydrogen-bonded 1,6-naphthyridines. Bioorg. Med. Chem. Lett. 2001, 11, 103-105.
7. Zhuang, L.; Wai, J. S.; Embrey, M. W.; Fisher, T. E.; Egbertson, M. S.; Payne, L. S.; Guare, J. P.; Vacca, J. P.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Witmer, M. V.; Moyer, G.; Schleif, W. A.; Gabryelski, L. J.; Leonard, Y. M.; Lynch, J. J.; Michelson, S. R.; Young, S. D. Design and synthesis of 8-hydroxy-[1,6]naphthyridines as novel inhibitors of HIV-1 integrase in vitro and infected cells. J. Med. Chem. 2003, 46, 453-456.
8. Bihlmayer, G. A.; Derflinger, G.; Derkosch, J.; Polansky, O. E. Monatsh. Chem. 1967, 98, 564.
9. Cassis, R.; Tapia, R.; Valderrama, J. A. Synthesis of 4(1H)-quinolone by thermolysis of arylaminomethylene meldrum's acid derivatives. Synth. Commun. 1985, 15 (2), 125-133.
10. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th edn.; Blackwell: Oxford, 2000; p. 134.
11. Lappin, G. R. Cyclization of 2-aminopyridine derivatives. 1: Substituted ethyl 2-pyridylaminomethylenemalonates. J. Am. Chem. Soc. 1948, 70, 3348.
12. Bassin, J. P.; Cremlyn, R. J.; Swinbourne, F. J. Chlorosulfonation of aromatic and hetero-aromatic system. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 46, 245-275.
13. Shukurov, S. S.; Kukaniev, M. A.; Nasyrov, I. M.; Zakharov, K. S.; Karakhanov, R. A. Electrophilic substitution in 2-bromo-7-methyl-5H-1,3,4- thiadiazolo[3,2,-a]pyrimidin-5-one. Russ. J. Gen. Chem. 1993, 63 (10), 1610-1611.