Synthesis of novel thieno- and pyrrolo[2,3-d]pyrimidines peri-fused with pyrimidine, 1,4-diazepine and 1,4-thiazepine rings

Synthesis

Volumn , Issue 9, 2003, Pages 1377-1382

  Tumkevicius, Sigitas ^a   Sarakauskaite, Zivile ^a   Masevicius, Viktoras ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

1 thia 3,5,6,9 tetraazabenz cd azulenes; 2,3,5,6,9 pentaazabenz cd azulenes; 6 thia 1,3,5,9 tetraazabenz cd azulene; Amino acids; Azaacenaphthylenes; Cyclisations; Heterocycles

Indexed keywords

ACYLATION; CHLORINE COMPOUNDS; ESTERS; FORMALDEHYDE; HEATING; NITROGEN COMPOUNDS; POTASH;

ETHYL ORTHOFORMATES;

SYNTHESIS (CHEMICAL);

2,3,5,6,9 PENTAAZABENZ[CD]AZULENE; 5 AMINO 4 (ETHOXYCARBONYLMETHYLTHIO)PYRROLO[2,3 D]PYRIMIDINE; 5 AMINO 4 CHLOROPYRROLO[2,3 D]PYRIMIDINE; 6 CHLORO 4 (ETHOXYCARBONYLMETHYLAMINO) 2 METHYLTHIOPYRIMIDINE 5 CARBONITRILE; 6 CHLORO 4 [N (METHOXYCARBONYLMETHYL) N METHYLAMINO] 2 METHYLTHIOPYRIMIDINE 5 CARBONITRILE; 6 THIA 2,3,5,9 TETRAAZABENZ[CD]AZULENE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAZEPINE DERIVATIVE; DIMETHYL SULFOXIDE; ESTER DERIVATIVE; ETHYL 5 (ETHOXYCARBONYLCARBONYLMETHYL) 7 METHYLTHIO 5H 3,4 DIHYDRO 1 THIA 3,5,6,8 TETRAAZAACENAPHTHYLENE 2 CARBOXYLATE; ETHYL 5 (ETHOXYCARBONYLMETHYL) 7 METHYLTHIO 5H THIA 3,5,6,8 TETRAAZAACENAPHTHYLENE 2 CARBOXYLATE; ETHYL 5 AMINO 4 (ETHOXYCARBONYLMETHYLAMINO) 2 METHYLTHIOTHIENO[2,3 D]PYRIMIDINE 6 CARBOXYLATE; ETHYL 5 CHLOROACETYLAMINO 4 (ETHOXYCARBONYLMETHYLAMINO) 2 METHYLTHIOTHIENO[2,3 D]PYRIMIDINE 6 CARBOXYLATE; ETHYL 6 (ETHOXYCARBONYLMETHYL) 4 METHYLTHIO 8 OXO 6,7,8,9 TETRAHYDRO 2 THIA 3,5,6,9 TETRAAZABENZ[CD]AZULENE 1 CARBOXYLATE; METHYL 5 (CARBOXYMETHYL) 1 METHYL 7 METHYLTHIO 1,3,4,5 TETRAHYDRO 1,3,5,6,8 PENTAAZACENAPHTHYLENE 2 CARBOXYLATE; METHYL 5 (ETHOXYCARBONYLMETHYL) 1 METHYL 7 METHYLTHIO 1,5 DIHYDRO 1,3,5,6,8 PENTAAZAACENAPHTHYLENE 2 CARBOXYLATE; METHYL 5 AMINO 4 (ETHOXYCARBONYLMETHYLAMINO) 7 METHYL 2 METHYLTHIO 7H PYRROLO[2,3 D]PYRIMIDINE 6 CARBOXYLATE; METHYL 5 AMINO 4 (METHOXYCARBONYLMETHYLTHIO) 7 METHYL 2 METHYLTHIO 7H PYRROLO[2,3 D]PYRIMIDINE; METHYL 5 AMINO 4 CHLORO 7 METHYL 2 METHYLTHIO 7H PYRROLO[2,3 D]PYRIMIDINE 6 CARBOXYLATE; METHYL 5 CHLOROACETYLAMINO 4 (ETHOXYCARBONYLMETHYLAMINO) 7 METHYL 2 METHYLTHIO 7H PYRROLO[2,3 D]PYRIMIDINE 6 CARBOXYLATE; POTASSIUM CARBONATE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; SARCOSINE; THIAZEPINE DERIVATIVE; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HEATING;

EID: 0037561026     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40209     Document Type: Article

References (22)

1. Russel, R. K.; Press, J. B.; Rampulla, R. A.; McNally, J. J.; Falotico, R.; Keiser, J. A.; Bright, D. A.; Tobia, A. J. Med. Chem. 1988, 31, 1786.
2. Russel, R. K.; Rampulla, R. A.; Van Nievelt, C. E.; Klaubert, D. H. J. Heterocycl. Chem. 1990, 27, 1761.
3. Modica, M.; Santagati, M.; Santagati, A.; Cutuli, V.; Mangano, N.; Caruso, A. Pharmazie 2000, 55, 500.
4. Panico, A.; Cardile, V.; Santagati, A.; Gentile, B. Farmaco 2001, 56, 959.
5. Katada, J.; Iijima, K.; Muramatsu, M.; Takami, M.; Yasuda, E.; Hayashi, M.; Hattori, M.; Hayashi, Y. Biorg. Med. Chem. Lett. 1999, 9, 797.
6. Porcari, A. R.; Ptak, R. G.; Borysko, K. Z.; Breitenbach, J. M.; Vittori, S.; Wotring, L. L.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2000, 43, 2438.
7. El-Sherbenyl, M. A.; El-Ashmawy, M. B.; El-Emam, H. I.; Badria, F. A. Eur. J. Med. Chem. Chim. Ther. 1995, 30, 445.
8. Pauwels, R.; Andries, K.; Desmyter, J.; Schols, D.; Kukla, M. J.; Breslin, H. J.; Raeymaeckers, A.; Van Gelder, J.; Woestenborgs, R.; Haaykants, J.; Schellekens, K.; Janssen, M. A. C.; De Clercq, E.; Jannsen, P. A. J. Nature (London) 1990, 343, 470.
9. Bellarosa, D.; Antonelli, G.; Bambacioni, F.; Giannotti, D.; Viti, G.; Nannicini, R.; Giachetti, A.; Dianzani, F.; Witvrouw, M.; Pauwels, R.; Desmyter, J.; De Clercq, E. Antiviral Res. 1996, 30, 109.
10. Taylor, E. C.; Patel, H. H.; Sabitha, G.; Chaudhari, R. Heterocycles 1996, 43, 349.
11. Rosowsky, A.; Papoulis, T.; Queener, S. F. J. Med. Chem. 1997, 40, 3694.
12. Tumkevicius, S. Liebigs Ann. Chem. 1995, 1703.
13. Tumkevicius, S.; Pupeikyte, R. J. Chem. Res., Synop. 1995, 286.
14. Tumkevicius, S.; Kaminskas, A.; Kulbokaite, J. J. Chem. Res., Synop. 2000, 287.
15. Tumkevicius, S.; Agrofoglio, L. A.; Kaminskas, A.; Urbelis, G.; Zevaco, T. A.; Walter, O. Tetrahedron Lett. 2002, 43, 695.
16. Santilli, A. A.; Kim, D. H.; Wanser, S. V. J. Heterocycl. Chem. 1971, 8, 445.
17. Wang, Z.; Neidlein, R.; Krieger, C. Synthesis 2000, 255.
18. Clark, J.; Shahhet, M. S.; Korakas, D.; Varvounis, G. J. Heterocycl. Chem. 1993, 30, 1065.
19. Hirota, K.; Shirahashi, M.; Senda, S.; Yogo, M. J. Heterocyl. Chem. 1990, 27, 717.
20. Tumkevicius, S.; Masevicius, V. Khim. Geterotsikl. Soedin. 1999, 35, 1577; Chem. Abstr. 2000, 133, 164037.
21. Tumkevicius, S.; Masevicius, V. Khim. Geterotsikl. Soedin. 1999, 35, 1577; Chem. Abstr. 2000, 133, 164037.
22. Schram, K. H.; Townsend, L. B. Tetrahedron Lett. 1971, 49, 4757.