Facile Synthesis of Hydrazine Derivatives of 5H-Pyrrolo[3,4-b]pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline

Olga V. Hordiyenko; Igor V. Rudenko; Irina A. Zamkova; Oleksandr V. Denisenko; Angelina V. Biitseva; Axelle Arrault; Andrei A. Tolmachev

doi:10.1055/s-0033-1340042

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(24): 3375-3382
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

Olga V. Hordiyenko*

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

,

Igor V. Rudenko

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

,

Irina A. Zamkova

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

,

Oleksandr V. Denisenko

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

,

Angelina V. Biitseva

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

,

Axelle Arrault

^bLaboratoire de Chimie Physique Macromoléculaire, INPL, ENSIC, 1 rue Grandville, 54001 Nancy Cedex, France

,

Andrei A. Tolmachev

^aTaras Shevchenko National University of Kyiv, vul. Volodymyrs’ka, 64/13, Kyiv 01601, Ukraine Fax: +380(44)2351273 eMail: ov_hordiyenko@univ.kiev.ua

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Abstract

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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.

Key words

heterocycles - nitriles - cyclization - chemoselectivity - hydrazones

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Referenzen

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

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