Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Unexpected Synthesis of Novel Condensed Heteromacrocycles Ahmed H. M. Elwahy*, Ashraf A. Abbas, Refaie M. KassabChemistry Department, Faculty of Science, Cairo University, Giza, EgyptFax: +20(2)5727556; e-Mail: aelwahy@chem-sci.cairo.eun.eg; Recommend Article Abstract Buy Article All articles of this category Abstract Alkylation of 4-amino-1,2,4-triazol-3(2H)-thiones 9a-d with 2,3-bis(bromomethyl)quinoxaline (8) in absolute ethanol containing potassium hydroxide gave the corresponding bis(amines) 10a-d. Condensation of the latter with the appropriate aromatic aldehydes in refluxing acetic acid afforded the corresponding benzylideneamino derivatives 12a,b. On the other hand, reaction of the bis(amines) 10a-d with the bis(aldehydes) 13a-c in refluxing acetic acid under high dilution conditions did not lead to the formation of the corresponding macrocyclic Schiffs bases 14. Instead, the reaction gave the corresponding novel condensed heteromacrocycles 15a-f. Key words alkylation - bis(bromomethyl)quinoxaline - heteromacrocycles - bis(amines) - bis(aldehydes) Full Text References References 1 Zhang XX. Bradshaw JS. Izatt RM. Chem. Rev. 1997, 97: 3313 2 Bradshaw JS. Izatt RM. Acc. Chem. Res. 1997, 30: 338 3 Izatt JS. J. Incl. Phenom. 1997, 29: 197 4 Bradshaw JS. J. Incl. Phenom. 1997, 29: 221 5 Izatt RM. Pawlak K. Bradshaw JS. Bruening RL. Chem. Rev. 1991, 91: 1721 6 Weber E. Kohler HJ. Reuter H. J. Prakt. Chem. 1995, 337: 451 7 Radd JT. Bradshaw JS. Huszthy P. Izatt RM. J. Heterocycl. Chem. 1994, 31: 1047 8 Radd JT. Bradshaw JS. Huszthy P. Izatt RM. Dally NK. J. Heterocycl. Chem. 1998, 35: 1 9 Li Y. Thiemann T. Sawada T. Tashiro M. J. Chem. Soc., Perkin Trans. 1 1994, 2323 10 Kim HS. Koh YK. Choi JH. J. Heterocycl. Chem. 1998, 35: 177 11 Elshani S. Apgar P. Wang S. Wai CM. J. Heterocycl. Chem. 1994, 31: 1271 12 Elwahy AHM. Abbas AA. Tetrahedron 2000, 56: 885 13 Foerster S. Niclas HJ. Lukyanenko NJ. Z. Chem. 1985, 25: 102 14 Mtay MM. Cohn OM. Tetrahedron Lett. 1976, 79 15 Elwahy AHM. Tetrahedron 2000, 56: 897 16a Elwahy AHM. Abbas AA. Ibrahim YA. J. Chem. Res. (S) 1996, 183 16b Elwahy AHM. Abbas AA. Ibrahim YA. J. Chem. Res. (M) 1996, 1066 17 Hoggarth E. J. Chem. Soc. 1952, 4811 18a Ibrahim YA. Elwahy AHM. El-Kareish GMM. J. Chem. Res. (S) 1994, 414 18b Ibrahim YA. Elwahy AHM. El-Kareish GMM. J. Chem. Res. (M) 1994, 2321 19a Ibrahim YA. Elwahy AHM. Abbas AA. J. Chem. Res. (S) 1998, 548 19b Ibrahim YA. Elwahy AHM. Abbas AA. J. Chem. Res. (M) 1998, 2501 20a Elwahy AHM. J. Chem. Res. (S) 1995, 88 20b Elwahy AHM. J. Chem. Res. (M) 1995, 653 21a Elwahy AHM. J. Chem. Res. (S) 1999, 602 21b Elwahy AHM. J. Chem. Res. (M) 1999, 2582 22 Kataritzky AR. Handbook of Heterocyclic Chemistry Pergamon; Oxford: 1985. 23 Shaw BL. J. Am. Chem. Soc. 1975, 97: 3856 24 Rasshofer W. Vogtle F. Liebigs Ann. Chem. 1978, 552
