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Synthesis 2013; 45(24): 3375-3382
DOI: 10.1055/s-0033-1340042
DOI: 10.1055/s-0033-1340042
paper
Facile Synthesis of Hydrazine Derivatives of 5H-Pyrrolo[3,4-b]pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline
Further Information
Publication History
Received: 03 July 2013
Accepted after revision: 26 September 2013
Publication Date:
06 November 2013 (online)
Abstract
A convenient and efficient route for the chemoselective synthesis of carbohydrazide, arenesulfonylhydrazide, and thiosemicarbazone derivatives of 5H-pyrrolo[3,4-b]pyrazine and 1H-pyrrolo[3,4-b]quinoxaline from the corresponding dinitriles and substituted hydrazines was elaborated. The synthesis of starting pyrazine-2,3-dicarbonitrile was sufficiently improved by using concentrated HCl as a catalyst.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Zimcik P, Novakova V, Miletin M, Kopecky K. Makrogeterotsikly 2008; 1: 21 ; Chem. Abstr. 2010, 153, 232243
- 2a Ambroise A, Maiya BG. Inorg. Chem. 2000; 39: 4264
- 2b Kudrevich SV, van Lier JE, Galpern MG, Luk’yanets EA. Can. J. Chem. 1996; 74: 508
- 2c Kudrevich SV, van Lier JE. Can. J. Chem. 1996; 74: 1718
- 2d Freyer W. J. Prakt. Chem. 1994; 8: 693
- 2e Danzig MJ, Liang CY, Passaglia E. J. Am. Chem. Soc. 1963; 85: 668
- 3a Dini D, Hanack M, Ji W, Weizhe C. Mol. Cryst. Liq. Cryst. 2005; 431: 559
- 3b Dini D, Hanack M, Meneghetti M. J. Phys. Chem. B 2005; 109: 12691
- 3c Dini D, Hanack M, Egelhaaf H.-J, Sancho-Garcia JC, Cornil J. J. Phys. Chem. B 2005; 109: 5425
- 4 Kitamura A, Nomura K, Inagaki Y. Jpn Kokai Tokkyo Koho JP 2009218369, 2009 ; Chem. Abstr. 2009, 151, 415851.
- 5 Jang CK, Jaung JY. Mol. Cryst. Liq. Cryst. 2012; 563: 238
- 6 Tadokoro K, Shoji M, Nanba M. Jpn Kokai Tokkyo Koho JP 11166130, 1999 ; Chem. Abstr. 1999, 131, 80742.
- 7 Yamamoto H, Fujita T. Jpn Kokai Tokkyo Koho JP 2010225689, 2010 ; Chem. Abstr. 2010, 153, 492800.
- 8 Yanagimoto T, Yokoyama N, Yamada H. Jpn Kokai Tokkyo Koho JP 2004302242, 2004 ; Chem. Abstr. 2004, 141, 386482.
- 9 Brach PJ, Grammatica SJ, Ossanna OA, Weinberger L. J. Heterocycl. Chem. 1970; 7: 1403
- 10 Tsuda T, Fujishima K, Ueda H. Agric. Biol. Chem. 1981; 45: 2129
- 11 Kojima T, Nagasaki F, Ohtsuka Y. J. Heterocycl. Chem. 1980; 17: 455
- 12a Kulikov MA, Vorob’ev YuG, Berezina GR, Stepanenko VA. Russ. J. Gen. Chem. 2004; 74: 954
- 12b Neustroeva NR, Kulikov MA, Vorob’ev YuG, Smirnov RP. Russ. J. Gen. Chem. 1999; 69: 1836
- 12c Genda Y, Tomita N, Ito M, Kano S. Jpn Kokai Tokkyo Koho JP 54119531, 1979 ; Chem. Abstr. 1980, 92, 95632.
- 12d Inagaki M. Jpn. Kokai Tokkyo Koho JP 7304601, 1973 ; Chem. Abstr. 1973, 79, 147427.
- 13a Suzuki T, Katou N, Mitsuhashi K. J. Heterocycl. Chem. 1978; 15: 1451
- 13b Patel NR, Castle RN. J. Heterocycl. Chem. 1966; 3: 512
- 14a Rothkopf HW, Wöhrle D, Müller R, Koßmehl G. Chem. Ber. 1975; 108: 875
- 14b Heckmann H, Metz HJ. Patent PCT Int. Appl. WO 2004108836, 2004 ; Chem. Abstr. 2004, 142, 58224.
- 15a Ahmad AR, Mehta LK, Parrick J. J. Chem. Soc., Perkin Trans. 1 1996; 20: 2443
- 15b Monge A, Palop JA, Pinol A, Martinez-Crespo FJ, Narro S, Gonzalez M, Sainz Y, Lopez de Cerain A, Hamilton E, Barker AJ. J. Heterocycl. Chem. 1994; 31: 1135
- 16a Koksharova TG, Konyukhov VN, Pushkareva ZV, Pryakhina TA. Chem. Heterocycl. Compd. 1972; 2: 247
- 16b Moriconi EJ, Misner RE, Brady TE. J. Org. Chem. 1969; 34: 1651
- 16c Haddadin MJ, Isoidorides CH. Tetrahedron Lett. 1968; 4609
- 17 Hayashi E, Utsunomiya A. Yakugaku Zasshi 1975; 95: 774 ; Chem. Abstr. 1975, 83, 206203
- 18 Ried W, Lee C.-H, Bats JW. Liebigs Ann. Chem. 1989; 5: 497
- 19 Hordiyenko OV, Biitseva AV, Kornilov MYu, Brosse N, Hocquet A, Jamart-Grégoire B, Shishkin OV, Zubatyuk RI. Eur. J. Org. Chem. 2006; 2833
- 20 Rudenko IV, Kucherak AA, Tolmachev AA, Hordiyenko OV. Chem. Heterocycl. Compd. 2011; 47: 964
- 21a (BASF SE, Germany) Patent EP 2371219, 2011 ; Chem. Abstr. 2011, 155, 503363.
- 21b Mombelli P, Witschel MC, van Zijl AW, Geist JG, Rottmann M, Freymond C, Röhl F, Kaiser M, Illarionova V, Fischer M, Siepe I, Schweizer WB, Brun R, Diederich F. ChemMedChem 2012; 7: 151
- 22a Tsuzuki K, Tada M. J. Heterocycl. Chem. 1985; 22: 1365
- 22b Tsuzuki K, Tada M. J. Heterocycl. Chem. 1986; 23: 1299
- 23a Tada M, Shiono D, Tanaka S. ARKIVOC 2005; (xv): 39
- 23b Tada M, Wada M. J. Chem. Res. Synop. 2003; 648
- 23c Korzhenevskii AB, Koifman OI, Efimova SV. Russian Patent RU 2269530, 2006 ; Chem. Abstr. 2006, 144, 212579.
- 24a Tada M, Asawa Y, Igarashi M. J. Heterocycl. Chem. 1997; 34: 9373
- 24b Tada M, Shimamura T, Suzuki T. Heterocycles 2003; 60: 2511
- 25 Roussel O, Kestemont G, Tant J, De Halleux V, Gómez Aspe R, Levin J, Remacle A, Raluca Gearba I, Ivanov D, Lehmann M, Geerts Y. Mol. Cryst. Liq. Cryst. 2003; 396: 35
- 26 Jones RG, McLaughlin KC. Org. Synth. Coll. Vol. 4 . Wiley; New York: 1963: 824
- 27a Iijima C, Miyashita A. Chem. Pharm. Bull. 1990; 38: 661
- 27b Gal’pern MG, Luk’yanets EA. Zh. Vses. Khim. Obschchest. 1967; 12: 474 ; Chem. Abstr. 1968, 68, 2789
- 28 Iijima C. Yakugaku Zasshi 1989; 109: 18 ; Chem. Abstr. 1989, 111, 134085
- 29 Hermann K, Simchen G. Liebigs Ann. Chem. 1981; 2: 333
- 30a Popp FD. J. Heterocycl. Chem. 1974; 11: 79
- 30b Ghosh P, Mandal A. Green Chem. Lett. Rev. 2012; 5: 127
- 31a Begland RW, Hartter DR. J. Org. Chem. 1972; 37: 4136
- 31b Webster OW, Hartter DR, Begland RW, Sheppard WA, Cairncross A. J. Org. Chem. 1972; 37: 4133
- 32 Ogg RA, Bergstrom FW. J. Am. Chem. Soc. 1931; 53: 1846
- 33 Turov AV, Biitseva AV, Hordiyenko OV. J. Org. Pharm. Chem. 2006; 4: 74
- 34 Biitseva A, Groth U, Hordiyenko O. J. Heterocycl. Chem. 2013; 50: 1140
- 35 Sulphur Compounds. In Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds . Vol. 3. Barton DH. R, Ollis WD. Oxford; Pergamon Press: 1979