Browse > Article
http://dx.doi.org/10.5012/bkcs.2002.23.4.567

New Fused Quinoxalines : Synthesis and Reactions of Pyrimidothienoquinoxaline and Oxadizolylthienoquinoxalines  

Moustafa, Osama S.
Badr, Mahmoud Z.A.
El-Emary, Talaat I.
Publication Information
Abstract
Diazotization of 3-amino-2-ethoxycarbonylthieno[2,3-b]quinoxaline 1 gave the diazonium salt 2 which was reacted with SO2 and N-methylaniline to give sulfamoylquinoxaline derivatives 3-5. Imidazothienoquinoxaline 8 was obtained from the reaction of carboxylic acid hydrazide 6 with nitrous acid and followed by boilling the carboazide 7 in dry xylene. Also, compound 6 react with CH(OEt)3 to give aminopyrimidine 9 which was reacted with arylidene malonodinitrile, furfural and/or dimethoxy-tetrahydrofuran to afford compounds 10, 11 and/or 12 respectively. Refluxing of 6 with CS2 gave oxadiazolylthienoquinoxaline 13, reaction of 13 with hyrazine hydrate, CH(OEt)3, nitrous acid, CS2 and a-halocompounds to give 14-19.
Keywords
Synthesis; Diazotization; Heterocycles; Pyrimidothienoquinoxalines;
Citations & Related Records

Times Cited By Web Of Science : 8  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
연도 인용수 순위
1 Geies, A. A.; El-Deen, A. M. K.; Moustafa, O. S. Pharmazie1996, 52(6), 437.
2 Makino, K.; Kim, H. S.; Yoshihisa, K. J.Heterocycl. Chem. 1998, 35, 489.   DOI   ScienceOn
3 Zhu, Z.; Saluja, S.; Drach, C. J.; Townsend, L. P. J. of the ChineseChem. Soc. 1988, 45(4), 465.
4 Mange, A.; Palop, J. A.; Urbasos, I.; Fernandez-Alvarez, E. J.Heterocycl. Chem. 1989, 26, 1623.   DOI
5 Kaneko, C.; Katagiri, S. (Asahi Glass Co.Ltd), Japan Kokai Tokkyo Koho Jp. (patent) 1988, 62, 207, 264. [Chem. Abstr. 1988, 109, 231061f].
6 Hiramatsu, T.; Azuma, S.; Nakagawa, K.; Ichikawa, Y. (Teijin Ltd.) Japan Kokai Tokkyo Koho Jp. (patent), 1988, 62, 163, 263, [Chem. Abstr. 1988, 109, 73473k].
7 Badr, M. Z. A.; Mahgoub, S. A.; Moustafa, O. S. J. Chem. Soc.Pakestan 1993, 15, 264.
8 Moustafa, O. S. J. of the Chinese Chem. Soc. 2000, 47(2), 351.
9 Moustafa, O. S.; Badr, M. Z. A.; Kamel, E. M. Pharmazie 2000,55(12), 896.
10 El-Ashry, E. S. H.; Abdel-Rahman, A. A. H.; Rashed, N.;Rasheed, H. A. Pharmazie 1999, 54(12), 893.
11 Gozyo, S.; Kenzi, M.; Yoshihisa, K. Heterocycles 1988, 27, 2481.   DOI
12 Makino, K.; Kim, H. S.; Yoshihisa, K. J. Heterocycl. Chem.1998, 35, 321.
13 El-Hawash, S. A.; Habib, N. S.; Fanaki, N. H. Pharmazie 1999,54, 808.
14 Bindumhavan, V.; Prabhakar, B. C.; Kumar, C. D.; John, D. N.; Helmut, R. R. (Hoechst India Ltd.) Indian IN 167,425 (patent) 1993, [Chem. Abstr. 1993, 119, 117279q].
15 Yoo, H. W.; Yun-Sil, L.; Suh, M. E.; Kim, D. J.; Park, S. W. Arch.Pharm. 1998, 331, 10331.
16 Badr, M. Z. A.; Mahgoub, S. A.; Moustafa, O. S. Phosphorus,Sulfur and Silicon 1993, 79, 477.
17 Moustafa, O. S. Phosphorus, Sulfur and Silicon 1999, 155, 235.   DOI   ScienceOn
18 Moustafa, O. S. Phosphorus, Sulfur and Silicon 1997, 131, 49.   DOI   ScienceOn
19 Miguel, A. O.; Maria, J. M.; Francisco, J. M.; Yolanda, S.; Maria,E. M.; Adele, L. C.; Antonio, M. Eur. J. Med. Chem. Chim. Ther.2000, 35, 121.
20 Sainz, Y.; Montoya, M. E.; Martinez, F. J.; Ortega, M. A.; Lopez, A.; Monge, A. Arzniem. Forsch. 1999, 49, 55. [Chem. Abstr. 1999, 130, 3827P].