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

被引：6

作者：

Hordiyenko, Olga V. ^{[1
]}

Rudenko, Igor V. ^{[1
]}

Zamkova, Irina A. ^{[1
]}

Denisenko, Oleksandr V. ^{[1
]}

Biitseva, Angelina V. ^{[1
]}

Arrault, Axelle ^{[2
]}

Tolmachev, Andrei A. ^{[1
]}

机构：

[1] Taras Shevchenko Natl Univ Kyiv, UA-01601 Kiev, Ukraine

[2] ENSIC, INPL, Lab Chim Phys Macromol, F-54001 Nancy, France

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 24期

关键词：

heterocycles; nitriles; cyclization; chemoselectivity; hydrazones; HYDROGEN-CYANIDE CHEMISTRY; EXCITED-STATE; COMPLEXES; DIIMINOSUCCINONITRILE; DIAMINOMALEONITRILE; QUINOXALINES;

D O I：

10.1055/s-0033-1340042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3375 / 3382

页数：8

共 57 条

[1]

Ahmad A R, 1996, J CHEM SOC P1, V20, P2443

[2] Ruthenium(II) complexes of 6,7-dicyanodipyridoquinoxaline: Synthesis, luminescence studies, and DNA interaction [J].

Ambroise, A ;

Maiya, BG .

INORGANIC CHEMISTRY, 2000, 39 (19) :4264-4272

[3]

[Anonymous], 2011, EP 2371219, Patent No. 2371219

[4]

Barton D H R, 1979, COMPREHENSIVE ORGANI, V3

[5] HYDROGEN-CYANIDE CHEMISTRY .4. DIIMINOSUCCINONITRILE REACTIONS WITH NUCLEOPHILES, ACYL HALIDES, AND CARBONYL-COMPOUNDS [J].

BEGLAND, RW ;

HARTTER, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (25) :4136-4145

[6] A One-Pot Synthesis of 3-Amino-1H-isoindol-1-one thiazol-2-ylhydrazones [J].

Biitseva, Angelina ;

Groth, Ulrich ;

Hordiyenko, Olga .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) :1140-1145

[7]

Brach P.J., 1970, Heterocycl. Chem, V7, P1403

[8] PREPARATION AND ELECTRICAL CONDUCTIVITY OF COPPER TETRA-2,3-PYRIDINOPORPHYRAZINE AND COPPER TETRA-2,3-PYRAZINOPORPHYRAZINE [J].

DANZIG, MJ ;

LIANG, CY ;

PASSAGLIA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (06) :668-&

[9] Optical limiting of transition metal-phthalocyanine complexes: A photochromic effect involving the excited state of the conjugated molecule [J].

Dini, D ;

Hanack, M ;

Ji, W ;

Chen, WZ .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2005, 431 :559-574

[10] Synthesis of axially substituted tetrapyrazinoporphyrazinato metal complexes for optical limiting and study of their photophysical properties [J].

Dini, D ;

Hanack, M ;

Egelhaaf, HJ ;

Sancho-García, JC ;

Cornil, J .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (12) :5425-5432

← 1 2 3 4 5 6 →