Synthesis of a Novel Class of Azacrown Macrocycles and Lariat Crown Ethers Containing Two 1,2,4-Triazole Rings as Subunits

Abstract

Azacrown macrocycles were prepared in 70-76% yield by the condensation reaction of 1,2-, 1,3-, and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes with bisaldehydes in acetic acid under reflux. Reaction of two of these azacrown macrocycles with iodomethane and benzyl chloride furnished exclusively the target lariat macrocycles in good yields.

Key words

azacrown macrocycles - 1,2,4-triazole - thiols - bistri­azoles - lariat crown ethers

References

• 1 Pedersen CJ. J. Am. Chem. Soc.  1967,  89:  7017 
• 2 Pedersen CJ. J. Am. Chem. Soc.  1967,  89:  2495 
• 3 Gokel GW. Crown Ethers and Cryptands (Monographs in Supramolecular Chemistry)   The Royal Society of Chemistry; Cambridge: 1991. 3
• 4 Richard ED. Milton DG. J. Am. Chem. Soc.  1976,  98:  762 
• 5 Newkome GR. Sauer JD. Rober JM. Hager DC. Chem. Rev.  1977,  77:  513 
• 6a Gokel GW. Federes MF. In Comprehensive Heterocyclic Chemistry   Vol. 9:  Elsevier; Oxford: 1996.  p.863 
• 6b Weber E. Kontakte (Darmstadt)  1983,  38 
• 7a Bradshaw JS. J. Inclusion Phenom. Macrocyclic Chem.  1997,  29:  221 
• 7b Weber E. Kohler HJ. Reuter HJ. J. Org. Chem.  1991,  56:  1236 
• 8a Bradshaw JS. Huszthy P. McDaniel CW. Zhu CY. Dalley NK. Izatt RM. Lifson S. J. Org. Chem.  1990,  55:  3129 
• 8b Bradshaw JS. Thompson PK. Izatt RM. J. Heterocycl. Chem.  1984,  21:  897 
• 9a Collier CP. Mattersteig G. Wong EW. Luo Y. Beverly K. Sampaio J. Raymo FM. Stoddart JF. Heath JR. Science (Washington, D.C.)  2000,  289:  1172 
• 9b Jefferson EA. Swayze EE. Osgood SA. Miyaji A. Risen LM. Blyn LB. Bioorg. Med. Chem. Lett.  2003,  13:  1635 
• 9c Jian L. Tington L. Yongmei W. Eur. J. Med. Chem.  2008,  43:  19 
• 9d Huang ST. Kuo HS. Hsiao CL. Lin YL. Bioorg. Med. Chem.  2002,  10:  1947 
• 10 Chung KB. Tomoi M. J. Polym. Sci., Part A: Polym. Chem.  1992,  30:  1089 
• 11 Weber E. Vögtle F. Top. Curr. Chem.  1981,  98:  14 
• 12 Gokel GW. Trafton JE. Cation Binding by Lariat Ethers, In Cation Binding by Macrocycles   Inoue Y. Gokel GW. Marcel Dekker; New York: 1990.  p.253 ; see also p. 279
• 13 Foroughifar N. Mobinikhaledi A. Ebrahimi S. Moghanian H. Bodaghi Fard MA. Kalhor M. Tetrahedron Lett.  2009,  50:  836 
• 14a Pellisard D. Luis R. Tetrahedron Lett.  1972,  4589 
• 14b Overman LE. J. Org. Chem.  1972,  37:  4214 
• 15 Sharghi H. Eshghi H. Tetrahedron  1995,  51:  913 
• 16 Morphy RJ. Parker D. Alexander R. Bains A. Came AF. Eaton MAW. Harrison A. Millican A. Philipps A. Rhind SK. Tetmas R. Weatherby D. J. Chem. Soc., Chem. Commun.  1988,  156 
• 17 Jurczak J. Kasprzyh S. Satanski P. Stankiewicz T. Lipkowski P. Tetrahedron  1993,  49:  1478 
• 18a Tabushi I. Taniguchi Y. Kado H. Tetrahedron Lett.  1977,  1049 
• 18b Tabushi I. Okino H. Kuroda Y. Tetrahedron Lett.  1976,  4339 
• 19 Xu PF. Sun XW. Zhang LM. Zhang ZY. J. Chem. Res., Synop.  1999,  170 
• 20 Ibrahim YA. Elwahy AHM. Elkareish GMM. J. Chem. Res., Synop.  1994,  414