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Synthesis 2001(9): 1331-1336
DOI: 10.1055/s-2001-15233
PAPER
© Georg Thieme Verlag Stuttgart · New York

Allyl-Substituted Macrocyclic Crown Formazans: Promising Precursors for Polymer-Supported Macrocycles

Ashraf A. Abbas*, Ahmed H. M. Elwahy
Department of Chemistry, Faculty of Science, Cairo University, Giza, A. R. Egypt
Fax: (00202)5727556; e-Mail: ashraf@chem-sci.cairo.eun.eg;
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Publication History

Received 27 February 2001
Publication Date:
24 September 2004 (online)

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Abstract

The bisphenol 1 was obtained by reacting the amine hydrochloride 11 with cyanoacetic acid in aqueous sodium hydroxide solution. Thermal rearrangement of 1,5-bis(allyloxyphenyl)formazan (7) failed to give 1. Alkylation of the bis phenol 1 with 1,3-dibromopropane in basic solution under high dilution conditions gave the corresponding allyl-substituted macrocyclic formazan 2a in a very low yield. On the other hand, diazotization of the new bis amine hydrochloride 3a,b with NaNO2 in hydrochloric acid followed by coupling with the appropriate active methylene compounds furnished the corresponding macrocyclic formazans 2a-d. Compounds 3a ,b were obtained by first reacting the K-salt of 12 with the appropriate dihalides to give the corresponding bis acetamides 13 and 14, respectively. Subsequent acid hydrolysis of the latter afforded 3a,b in good yield.

Key words

alkylation - thermal rearrangement - diazotization - coupling - macrocyclic formazans

    References

  • 1 Ibrahim YA. Elwahy AHM. Abbas AA. Tetrahedron  1994,  50:  11489 
    CrossrefGoogle Scholar
  • 2 Katritzky AR. Belyakov SA. Durst HD. Tetrahedron Lett.  1994,  35:  6465 
    CrossrefGoogle Scholar
  • 3a Zolotov YuA. Niz"eva NV. Iono PV. Dziomko VM. Ostrovskaya VM. D"yakonova IA. Otkrytiya, Izobret., Prom. Obraztsy, Tovarnye Znaki  1983,  46:  16 
    Google Scholar
  • 4a Niz"eva NV. Ionov PV. Pletnev IV. Kumina DM. Ostrovskaya VM. D"yakonova IA. Zolotov YuA. Dokl. Akad. Nauk SSSR  1984,  274:  611 
    Google Scholar
  • 5a Zolotov YuA. Ionov VP. Bodnyav AV. Larikova GA. Niz"eva NV. Vlasova GE. Rybakova EV. Zh. Anal. Khim.  1982,  37:  1543 
    Google Scholar
  • 6a Isakova NV. Zolotov YuA. Ionov VP. Zh. Anal. Khim.  1989,  44:  1045 
    Google Scholar
  • 7a Lin IC, and Pirio M. inventors; U. S. Patent  4,742,010. 
  • 8a Dziomko VM. Ostrovskaya VM. Zhukova TE. Zhukova TE. Ryabokobylko YuS. Zh. Obshch. Khim.  1981,  51:  2324 
    Google Scholar
  • 9a Sitnikova RV. Krylova AN. Lab. Delo  1980,  3:  142 
    Google Scholar
  • 10a Misionzhnik EYu. Uzbekov MG. Ostrovskaya VM. Sitnikova GI. Avrustkii GYa. Neduva AA. Ettinger II. Lab. Delo  1990,  7:  19 
    Google Scholar
  • 11 Attiyat AS. Ibrahim YA. Christain GD. Microchem. J.  1988,  37:  114 
    CrossrefGoogle Scholar
  • 12 Attiyat AS. Ibrahim YA. Christain GD. Microchem. J.  1988,  37:  122 
    CrossrefGoogle Scholar
  • 13a Sitnikova RV. Krylova AN. Zelichenok SL. Dziomko VM. Ostrovskaya VM. Zhukova TE. Tolmacheva EI. Zh. Anal. Khim.  1982,  37:  611 
    Google Scholar
  • 14 Christain GD. Lithium  1990,  3:  181 
    Google Scholar
  • 15a Ostrovskaya VM. Sitnikova IG. Ryabokobylko YuS. Dziomko VM. Sitnikova RV. Avrutskii YaG. Neduva AA. Misionzhnik EYu. Otkrytiya, Izobret.  1989,  185 
    Google Scholar
  • 16a Kravchenko MS. Ostrovskaya VM. Fumarova MSh. Vysokochist. Veshchestva  1990,  152 
    Google Scholar
  • 17 Ibrahim YA. Elwahy AHM. Abbas AA. Heteroat. Chem.  1996,  7:  215 
    CrossrefGoogle Scholar
  • 18 Abbas AA. Tetrahedron  1998,  54:  12421 
    CrossrefGoogle Scholar
  • 19 Ibrahim YA. Elwahy AHM. Barsum NB. Abbas AA. Kella SK. Talanta  1998,  47:  1199 
    CrossrefGoogle Scholar
  • 20 Ibrahim YA. Barsum NB. Elwahy AHM. Kella SK. Supramol. Chem.  1998,  9:  5 
    Google Scholar
  • 21 Barsum NB. Kella SK. Elwahy AHM. Abbas AA. Ibrahim YA. Talanta  1998,  47:  1215 
    CrossrefGoogle Scholar
  • 22a Bogdal D. Pielichowski J. Polimery  1997,  42:  651 
    Google Scholar
  • 23a Pilizota V. Khim. Ind.  1998,  47:  93 
    Google Scholar
  • 24a Lu X. Zhang B. Song M. He B. Lizi Jiaohuan. Yu Xifu  1996,  12:  271 
    Google Scholar
  • 25a Ergozhin EE. Kurmanaliev MK. Izv. Nats. Akad. Nauk Resp. Kaz., Ser. Khim.  1995,  111:  4 
    Google Scholar
  • 26 Yokota K. Kakuchi T. Taniguchi Y. Takada Y. Makromol. Chem., Rapid Commun.  1985,  6:  155 
    CrossrefGoogle Scholar
  • 27 Hodge P. Khoshdel E. Waterhouse J. J. Chem. Soc., Perkin Trans. 1  1984,  2451 
    CrossrefGoogle Scholar
  • 28 Tiffany BD. J. Am. Chem. Soc.  1948,  70:  592 
    CrossrefGoogle Scholar
  • 29a Ibrahim YA. Elwahy AHM. J. Chem. Res., Synop.  1993,  252 
    Google Scholar
  • 29b Ibrahim YA. Elwahy AHM. J. Chem. Res., Miniprint  1993,  1684 
    Google Scholar