Preparation of 3,5-Disubstituted 1,2,4-Oxadiazoles by Reactions of Nitrilium Salts with Amide Oximes

Ahmed H. Moustafa

doi:10.1055/s-2003-38682

PAPER

Preparation of 3,5-Disubstituted 1,2,4-Oxadiazoles by Reactions of Nitrilium Salts with Amide Oximes

Ahmed H. Moustafa*
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
e-Mail: ah_hu_mostafa@yahoo.com;

Abstract

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Abstract

The reaction of N-alkyl- and N-arylnitrilium salts 1a,d,g,j with the amide oximes 2a-c furnished the new iminium salts 3a-k (76-93%). On heating, compounds 3a-c cyclized to salts, which were transformed with base to the 3,5-disubstituted 1,2,4-oxadiazoles 4a-c in good yields (ca. 80%).

Key words

nitrilium salts - amide oxime - iminium salts - oxadiazoles

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References

<A NAME="RP00803SS-1">1</A> Klages F. Grill W. Liebigs Ann. Chem. 1955, 594: 21

<A NAME="RP00803SS-2">2</A> Meerwein H. Angew. Chem. 1955, 67: 374

<A NAME="RP00803SS-3">3</A> Meerwein H. Laasch P. Mersch R. Spille J. Chem. Ber. 1956, 89: 209

<A NAME="RP00803SS-4">4</A> Voges A. Hamed A. El-Badry AA. Ismail AE. Jochims JC. Synthesis 1995, 235

<A NAME="RP00803SS-5">5</A> Kabuß S. Angew. Chem. Int. Ed. Engl. 1966, 5: 675 ; Angew. Chem., 1966, 78, 714

<A NAME="RP00803SS-6">6</A> Olah GA. Gupta BG. Narang SC. Synthesis 1979, 274

<A NAME="RP00803SS-7">7</A> Vilsmeier E. Schneider R. Schütz J. Liebigs Ann. Chem. 1980, 1064

<A NAME="RP00803SS-8">8</A> Schrobilgen GJ. J. Chem. Soc., Chem. Commun. 1988, 863

<A NAME="RP00803SS-9">9</A> Glocker MO. Shrestha-Dawadi PB. Küchler-Krischun J. Hofmann J. Fischer H. Jochims JC. Chem. Ber. 1993, 126: 1859

<A NAME="RP00803SS-10">10</A> Johnson F. Madronero R. Adv. Heterocycl. Chem. 1966, 6: 95

<A NAME="RP00803SS-11">11</A> Johnson F. Duquette LG. Parker WL. Nasutavicus WA. J. Org. Chem. 1974, 39: 1434

<A NAME="RP00803SS-12">12</A> Zielinski W. Heterocycles 1985, 23: 1639

<A NAME="RP00803SS-13">13</A> Borodaev SV. Zubkova OV. Luk"yanov SM. Zh. Org. Khim. 1988, 24: 2330

<A NAME="RP00803SS-14">14</A> Schinzer D. Bo Y. Angew. Chem. Int. Ed. Engl. 1991, 30: 687 ; Angew. Chem. 1991, 103, 727

<A NAME="RP00803SS-15">15</A> Luk’yanov SM. Borodaev SV. Zubkova OV. Zh. Org. Khim. 1992, 28: 2577

<A NAME="RP00803SS-16A">16a</A> Ibrahim YA. Moustafa AH. J. Chem. Res., Synop. 1999, 254

<A NAME="RP00803SS-16B">16b</A> Ibrahim YA. Moustafa AH. J. Chem. Res., Miniprint 1999, 1231

<A NAME="RP00803SS-17">17</A> Moustafa AH. Hitzler MG. Lutz M. Jochims JC. Tetrahedron 1997, 53: 625

<A NAME="RP00803SS-18">18</A> Moustafa AH. Wirschun W. Freyhardt CC. Jochims JC. Abu-El-Halawa R. J. Prakt. Chem. 1997, 339: 615

<A NAME="RP00803SS-19">19</A> Grundmann C. Dean JM. J. Org. Chem. 1965, 30: 2809

<A NAME="RP00803SS-20">20</A> Abu-El-Halawa R. Shrestha-Dawadi PB. Jochims JC. Chem. Ber. 1993, 126: 109

<A NAME="RP00803SS-21">21</A> Hitzler MG. Freyhardt CC. Jochims JC. J. Prakt. Chem. 1996, 338: 243

<A NAME="RP00803SS-22">22</A> Chiou S. Shine HJ. J. Heterocycl. Chem. 1989, 26: 125

<A NAME="RP00803SS-23">23</A> Kabakchi EV. Il’in VV. Ignatenko AV. Ponomarenko VA. Izvest. Akad. Nauk, Ser. Khim. 1992, 41: 1863

<A NAME="RP00803SS-24">24</A> Ainsworth C. Buting WE. Davenport J. Callender ME. McCowen MC. J. Med. Chem. 1967, 10: 208

<A NAME="RP00803SS-25">25</A> Waters WA. J. Chem. Soc. 1937, 113

<A NAME="RP00803SS-26">26</A> Vargha L. Gönczy F. J. Med. Chem. 1967, 10: 208

<A NAME="RP00803SS-27">27</A> Charles R. David S. Chem. Ber. 1886, 19: 1487

<A NAME="RP00803SS-28">28</A> Jochims JC. Abu-El-Halawa R. Jibril I. Huttner G. Chem. Ber. 1984, 117: 1900

<A NAME="RP00803SS-29">29</A> Jochims JC. Hehl S. Herzberger S. Synthesis 1990, 1128

<A NAME="RP00803SS-30">30</A> Kaugars G. Watt W. J. Heterocycl. Chem. 1993, 30: 497

<A NAME="RP00803SS-31">31</A> Molina P. Alajarin M. Ferao A. Synthesis 1986, 843

<A NAME="RP00803SS-32">32</A> da Costa Leite LFC. Srivastava RM. Cavalcanti AP. Bull. Soc. Chim. Belg. 1989, 98: 203