Convenient Method for the Synthesis of Macrocyclic Teteraamides, Acyclic Diamides, their Lariat Derivatives and Bis-macrocyclic Tetraamides

Abstract

The macrocyclic tetraamides 8a-e were obtained in good yields by bis-alkylation of the potassium salts of the appropriate bis-phenols 7a-c with the dihalo compounds 2a,b. Similarly, macrocyclic tetraamides with pendant hydroxy group 18a,b were prepared by the nucleophilic reaction of the potassium salts of 7a,b with the dihalo compound 10. Acylation of 18a,b with chloroacetyl chloride gave the corresponding ester 19a,b. Compounds 19a,b reacted with different secondary amines to afford the corresponding lariat macrocycles 20a-d and novel bis-macrocycle 21 in 50-65% yield.

Key words

macrocyclic teteraamides - acyclic diamides - lariat macrocycles - bis-macrocyclic tetraamides

References

• 1 Irie S. Yamamoto M. Kishikawa K. Kohmoto S. Yamada K. Synthesis  1995,  1179 
• 2 Fujita T. Lehn JM. Tetrahedron Lett.  1988,  29:  1122 
• 3 Cram DJ. Angew. Chem., Int. Ed. Engl.  1986,  25:  1035 
• 4 Grammenudi S. Vögtle F. Angew. Chem., Int. Ed. Engl.  1986,  25:  1122 
• 5 Pioget T. Duriez MC. Picard C. Cazaux L. Tisnes P. Tetrahedron  1992,  48:  4359 
• 6 Cazaux L. Duriez MC. Picard C. Tisnes P. Tetrahedron Lett.  1989,  30:  1369 
• 7 Cazaux L. Picard C. Pigot T. Tisnes P. Tetrahedron Lett.  1991,  32:  919 
• 8 Nakatsuji Y. Kobayashi H. Okahara M. Matsushima K. Chem. Lett.  1982,  1571 
• 9 Maruizumi T. Wegmann D. Suter G. Ammann D. Simon W. Mikrochim. Acta  1986,  63:  2271 
• 10 Kataky R. Nicholson PE. Paeker D. Covington AK. The Analyst  1991,  116:  135 
• 11 Erne D. Stojanac N. Ammann D. Hofstetter P. Pretsch E. Simon W. Helv. Chim. acta  1980,  63:  2271 
• 12 Schefer U. Ammann D. Pretsch E. Oesch U. Simon W. Anal. Chem.  1986,  58:  2282 
• 13 Collins TJ. Kostka KL. Munck E. Uffelman ES. J. Am. Chem. Soc.  1990,  112:  5637 
• 14 Kimura E. Pure Appl. Chem.  1989,  61:  823 
• 15 Kimura E. Kurogi Y. Wada S. Shionoya M. J. Chem. Soc., Chem. Commun.  1989,  781 
• 16 Gordon W, Scott W, and Collins TJ. inventors; US Patent  6051704.  ; Chem. Abstr. 2000, 132, 273412
• 17 Kumar S. Hundal MS. Hundal G. Kaur N. Singh H. Tetrahedron  1997,  53:  10841 
• 18 Kumar S. Hundal G. Kaur N. Hundal MS. Singh H. Tetrahedron Lett.  1997,  38:  131 
• 19 Krakowiak KE. Bradshaw JS. Zamecka-Krakowiak DJ. Chem. Rev.  1989,  89:  929 
• 20 Dietrich B. In Comprehensive Supramolecular Chemistry   Gokel GW. Pergamon; New York: 1996.  p.153-212  
• 21 Krakowiak KE. Bradshaw JS. Izatt RM. J. Org. Chem.  1990,  55:  3364 
• 22 Metzger E. Ammann D. Schefer U. Pretsch E. Simon W. Chimia  1984,  38:  440 
• 23 Metzger E. Ammann D. Asper R. Simon W. Anal. Chem.  1986,  58:  132 
• 24 Kataky R. Nicholson PE. Paeker D. Tetrahedron Lett.  1989,  30:  4554 
• 25 Gokel GW. Dishong DM. Diamond CJ. J. Chem. Soc., Chem. Commun.  1980,  1053 
• 26 Gokel GW. Chem. Soc. Rev.  1992,  21:  39 
• 27 Schultz RA. White BD. Dishong DM. Arnold KA. Gokel GW. J. Am. Chem. Soc.  1985,  107:  6659 
• 28 Gokel GW. Arnold KA. Cleary T. Friese R. Gatto V. Goli D. Hanlon C. Kim M. Miller S. Ouchi M. Posey I. Sandler A. Viscariello A. White B. Wolfe J. Yoo H. In ACS Symposium Series, 326: Phase-Transfer Cataysis - New Chemistry, Catalysts, and Applications   Starks CM. ACS; Washington DC: 1987.  p.24 
• 29 Goto Y. Kohno Y. Fukuda W. Tomoi Y. J. Polymer Science: Part A: Polymer Chemistry  1994,  32:  1543 
• 30 Elwahy AHM. Abbas AA. Tetrahedron  2000,  56:  885 
• 31 Ibrahim YA. Elwahy AHM. Abass AA. J. Chem. Res., Synop.  1998,  548 
• 32 Ibrahim YA. Elwahy AHM. Abass AA. Kassab RM. J. Chem. Res., Synop.  1999,  522 
• 33 Elwahy AHM. Abass AA. Kassab RM. Heteroatom Chem.  2003,  14:  551 
• 34 Abbas AA. Tetrahedron  1997,  54:  12421 
• 35 Ibrahim YA. Elwahy AHM. Synthesis  1993,  503 
• 36 Wong KH. Bourgoin M. Smid J. J. Chem. Soc., Chem. Commun.  1974,  715 
• 37 Bourgoin M. Wong KH. Hui JY. Smid J. J. Am. Chem. Soc.  1975,  97:  3462 
• 38 Ibrahim YA. Elwahy AHM. Abbas AA. Tetrahedron  1994,  50:  11489 
• 39 Ibrahim YA. Elwahy AHM. Barsom BN. Abbas AA. Khella SK. Talanta  1998,  47:  1199 
• 40 Djurendic EA. Sauranyj TM. Miljkovic DA. Coll. Czech. Chem. Commun.  990,  55:  1763