Unexpected Synthesis of Novel Condensed Heteromacrocycles

Ahmed H. M. Elwahy; Ashraf A. Abbas; Refaie M. Kassab

doi:10.1055/s-2002-19809

PAPER

Unexpected Synthesis of Novel Condensed Heteromacrocycles

Ahmed H. M. Elwahy*, Ashraf A. Abbas, Refaie M. Kassab
Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt
Fax: +20(2)5727556; e-Mail: aelwahy@chem-sci.cairo.eun.eg;

Abstract

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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)

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References

<A NAME="RZ08401SS-1">1</A> Zhang XX. Bradshaw JS. Izatt RM. Chem. Rev. 1997, 97: 3313

<A NAME="RZ08401SS-2">2</A> Bradshaw JS. Izatt RM. Acc. Chem. Res. 1997, 30: 338

<A NAME="RZ08401SS-3">3</A> Izatt JS. J. Incl. Phenom. 1997, 29: 197

<A NAME="RZ08401SS-4">4</A> Bradshaw JS. J. Incl. Phenom. 1997, 29: 221

<A NAME="RZ08401SS-5">5</A> Izatt RM. Pawlak K. Bradshaw JS. Bruening RL. Chem. Rev. 1991, 91: 1721

<A NAME="RZ08401SS-6">6</A> Weber E. Kohler HJ. Reuter H. J. Prakt. Chem. 1995, 337: 451

<A NAME="RZ08401SS-7">7</A> Radd JT. Bradshaw JS. Huszthy P. Izatt RM. J. Heterocycl. Chem. 1994, 31: 1047

<A NAME="RZ08401SS-8">8</A> Radd JT. Bradshaw JS. Huszthy P. Izatt RM. Dally NK. J. Heterocycl. Chem. 1998, 35: 1

<A NAME="RZ08401SS-9">9</A> Li Y. Thiemann T. Sawada T. Tashiro M. J. Chem. Soc., Perkin Trans. 1 1994, 2323

<A NAME="RZ08401SS-10">10</A> Kim HS. Koh YK. Choi JH. J. Heterocycl. Chem. 1998, 35: 177

<A NAME="RZ08401SS-11">11</A> Elshani S. Apgar P. Wang S. Wai CM. J. Heterocycl. Chem. 1994, 31: 1271

<A NAME="RZ08401SS-12">12</A> Elwahy AHM. Abbas AA. Tetrahedron 2000, 56: 885

<A NAME="RZ08401SS-13">13</A> Foerster S. Niclas HJ. Lukyanenko NJ. Z. Chem. 1985, 25: 102

<A NAME="RZ08401SS-14">14</A> Mtay MM. Cohn OM. Tetrahedron Lett. 1976, 79

<A NAME="RZ08401SS-15">15</A> Elwahy AHM. Tetrahedron 2000, 56: 897

<A NAME="RZ08401SS-16A">16a</A> Elwahy AHM. Abbas AA. Ibrahim YA. J. Chem. Res. (S) 1996, 183

<A NAME="RZ08401SS-16B">16b</A> Elwahy AHM. Abbas AA. Ibrahim YA. J. Chem. Res. (M) 1996, 1066

<A NAME="RZ08401SS-17">17</A> Hoggarth E. J. Chem. Soc. 1952, 4811

<A NAME="RZ08401SS-18A">18a</A> Ibrahim YA. Elwahy AHM. El-Kareish GMM. J. Chem. Res. (S) 1994, 414

<A NAME="RZ08401SS-18B">18b</A> Ibrahim YA. Elwahy AHM. El-Kareish GMM. J. Chem. Res. (M) 1994, 2321

<A NAME="RZ08401SS-19A">19a</A> Ibrahim YA. Elwahy AHM. Abbas AA. J. Chem. Res. (S) 1998, 548

<A NAME="RZ08401SS-19B">19b</A> Ibrahim YA. Elwahy AHM. Abbas AA. J. Chem. Res. (M) 1998, 2501

<A NAME="RZ08401SS-20A">20a</A> Elwahy AHM. J. Chem. Res. (S) 1995, 88

<A NAME="RZ08401SS-20B">20b</A> Elwahy AHM. J. Chem. Res. (M) 1995, 653

<A NAME="RZ08401SS-21A">21a</A> Elwahy AHM. J. Chem. Res. (S) 1999, 602

<A NAME="RZ08401SS-21B">21b</A> Elwahy AHM. J. Chem. Res. (M) 1999, 2582

<A NAME="RZ08401SS-22">22</A> Kataritzky AR. Handbook of Heterocyclic Chemistry Pergamon; Oxford: 1985.

<A NAME="RZ08401SS-23">23</A> Shaw BL. J. Am. Chem. Soc. 1975, 97: 3856

<A NAME="RZ08401SS-24">24</A> Rasshofer W. Vogtle F. Liebigs Ann. Chem. 1978, 552