Tandem vicarious nucleophilic substitution of hydrogen/intramolecular Diels-Alder reaction of 1,2,4-triazines into functionalized cycloalkenopyridines1

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 4, 2002, Pages 463-466

  Branowska, Danuta ^a   Ostrowski, Stanisław ^a   Rykowski, Andrzej ^a  

^a SIEDLCE UNIVERSITY OF NATURAL SCIENCES AND HUMANITIES   (Poland)

Author keywords

1,2,4 triazine; Cycloalkenopyridine; Diels Alder reaction; Vicarious nucleophilic substitution

Indexed keywords

2 PHENYL 5,6,7,8 TETRAHYDROQUINOLINE 8 SULFONIC ACID 2,2 DIMETHYLPROPYL ESTER; 2 PHENYL 5,6,7,8 TETRAHYDROQUINOLINE 8 SULFONIC ACID DIMETHYLAMIDE; 2 PHENYL 7 PHENYLSULFONYL 6,7 DIHYDRO 5H [1]PYRIMIDINE; 2 PHENYL 8 (PYRROLIDINE 1 SULFONYL) 5,6,7,8 TETRAHYDROQUINOLINE; 2 PHENYL 8 (TOLUENE 4 SULFONYL) 5,6,7,8 TETRAHYDROQUINOLINE; 2,3 CYCLOPENTENOPYRIDINE; 3 METHYLSULFANYL 1 PHENYL 7 PHENYLSULFONYL 6,7 DIHYDRO 5H [2]PYRIMIDINE; 3 METHYLSULFANYL 1 PHENYL 8 PHENYLSULFONYL 5,6,7,8 TETRAHYDROISOQUINOLINE; 3,4 CYCLOPENTENOPYRIDINE; 7 (MORPHOLINE 4 SULFONYL) 2 PHENYL 6,7 DIHYDRO 5H [1]PYRIMIDINE; 8 (MORPHOLINE 4 SULFONYL) 2 PHENYL 5,6,7,8 TETRAHYDROQUINOLINE; ESTER DERIVATIVE; METHYL GROUP; NITROGEN; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SULFONAMIDE; SULFONIC ACID DERIVATIVE; SULFUR DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; 1,2,4 TRIAZINE; 1,2,4-TRIAZINE; HYDROGEN; TRIAZINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION KINETICS; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH TEMPERATURE PROCEDURES; HYDROGEN BOND; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE; CHEMISTRY;

ALKYLATION; HYDROGEN; PYRIDINES; TRIAZINES;

EID: 0036545377     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.463     Document Type: Article

References (18)

1. Part 17 in "1,2,4-Triazines in Organic Synthesis." For part 16, see Rykowski A., Wolińska E., van der Plas H. C., Khim. Geterotsikl. Soedin. 2001, 1549-1555.
2. Thummel R. P., "Carbocyclic Annelated Pyridines," in "Pyridine and Its Derivatives," Part 5, ed. by Newkome G. R., Vol. 14 in the series "The Chemistry of Heterocyclic Compounds," ed. by Weissberger A., Taylor E. C., Wiley-Interscience, New York, 1984, pp. 253-445.
3. Taylor E. C., Macor J. E., French L. G., J. Org. Chem., 56, 1807-1812 (1991).
4. Charushin V. N., Alexeev S. G., Chupakhin O. N., van der Plas H. C., Adv. Heterocycl. Chem., 46, 74-142 (1989).
5. a) Rykowski A., Makosza M., Liebigs Ann. Chem., 1988, 627-631;
6. b) Makosza M., Wojciechowski K., Heterocycles, 54, 445-474 (2001).
7. Jung M. E., Synlett, 1990, 186-190.
8. Brown R. E., Lustgarten D. M., Stanaback R. J., Osborne M. W., Meltzer R. I., J. Med. Chem., 7, 232-235 (1964).
9. Meyers A. I., Schneller J., Ralhan N. K., J. Org. Chem., 28, 2944-2950 (1963).
10. Neilands L., Khim. Geterotsikl. Soedin., 1970, 647-650;
11. Chem.Abstr., 73: 77013w (1970).
12. Dewar M. J. S., J. Chem. Soc., 1944, 615-619.
13. The samples are under investigation for tuberculostatic activity at the Southern Research Institute, Birmingham, U.S.A.
14. Ma̧kosza M., Goliński J., Baran J., J. Org. Chem., 49, 1488-1494 (1984).
15. Ma̧kosza M., Danikiewicz W., Wojciechowski K., Liebigs Ann. Chem., 1987, 711-715.
16. Christensen L. W., Seaman J. E., Truce W. E., J. Org. Chem., 38, 2243-2245 (1973).
17. Jacobsen H. J., Senning A., Kaae S., Acta Chem. Scand., 25, 3031-3035 (1971).
18. Ma̧kosza M., Goliński J., Synthesis, 1983, 1023-1025.