Synthesis and reactivity of novel pyrrolo[1,2-a]pyrazine derivatives

被引：5

作者：

Voievudskyi, Maxim ^{[1
]}

Astakhina, Valeriia ^{[1
]}

Kryshchyk, Oxana ^{[1
]}

Petuhova, Olena ^{[2
]}

Shyshkina, Svetlana ^{[3
,4
]}

机构：

[1] Ukrainian State Univ Chem Technol, Dnepropetrovsk, Ukraine

[2] Dnipropetrovsk Natl Univ O Honchar, Dnepropetrovsk, Ukraine

[3] Natl Acad Sci Ukraine, SSI Inst Single Crystals, Kharkov, Ukraine

[4] Kharkov Natl Univ, Kharkov, Ukraine

来源：

MONATSHEFTE FUR CHEMIE | 2016年 / 147卷 / 04期

关键词：

Azomethine; Cyclizations; Crystal structure; Schiff bases; POTENT; AGONISTS; AS-3201;

D O I：

10.1007/s00706-015-1619-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This research describes the utility of ethyl 2-amino-6,8-dimethyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo-[1,2-a]pyrazine-7-carboxylate as a key starting material for synthesis of novel analogues of natural alkaloid peramine. This heterocyclic compound was synthesized by the reaction of corresponding N-alkylpyrrole with hydrazine hydrate in good yield. In further step, chemical reactivity of N-aminopiperazine was studied towards some electrophilic reagents such as carbonyl compounds, triethyl orthoformate, nitrous acid, acetylenedicarboxylic acid. The new compounds were characterized by H-1 and C-13 NMR, IR, elemental analysis, and X-ray crystallographic study.

引用

页码：783 / 789

页数：7

共 12 条

[1]

Abiati G, 2006, SYNLETT, V73

[2] Pyrrolo[1,2-a]pyrazine and pyrazolo[1,5-a]pyrazine: Novel, potent, and selective series of Vasopressin1b receptor antagonists [J].

Arban, Roberto ;

Bianchi, Federica ;

Buson, Alberto ;

Cremonesi, Susanna ;

Di Fabio, Romano ;

Gentile, Gabriella ;

Micheli, Fabrizio ;

Pasquarello, Alessandra ;

Pozzan, Alfonso ;

Tarsi, Luca ;

Terreni, Silvia ;

Tonelli, Federica .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) :5044-5049

[3] Long-term effects of ranirestat (AS-3201) on peripheral nerve function in patients with diabetic sensorimotor polyneuropathy [J].

Bril, V ;

Buchanan, RA .

DIABETES CARE, 2006, 29 (01) :68-72

[4] Synthesis and anticonvulsant activity of novel 2,6-diketopiperazine derivatives. Part 1: Perhydropyrrole[1,2-a]pyrazines [J].

Dawidowski, Maciej ;

Herold, Franciszek ;

Chodkowski, Andrzej ;

Kleps, Jerzy ;

Szulczyk, Pawel ;

Wilczek, Marcin .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (10) :4859-4869

[5]

Gudasheva T.A., 1996, PHARM CHEM J, V30, P562

[6] Novel, highly potent aldose reductase inhibitors:: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-α]pyrazine-4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone (AS-3201) and its congeners [J].

Negoro, T ;

Murata, P ;

Ueda, S ;

Fujitani, B ;

Ono, Y ;

Kuromiya, A ;

Komiya, M ;

Suzuki, K ;

Matsumoto, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (21) :4118-4129

[7]

Olson K, 1979, ACTA CHEM SCAND B, V33, P125

[8] Novel selective and partial agonists of 5-HT3 receptors .1. Synthesis and biological evaluation of piperazinopyrrolothienopyrazines [J].

Rault, S ;

Lancelot, JC ;

Prunier, H ;

Robba, M ;

Renard, P ;

Delagrange, P ;

Pfeiffer, B ;

Caignard, DH ;

GuardiolaLemaitre, B ;

Hamon, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (10) :2068-2080

[9] Discovery of potent and selective histamine H3 receptor inverse agonists based on the 3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one scaffold [J].

Richter, H. G. F. ;

Freichel, C. ;

Huwyler, J. ;

Nakagawa, T. ;

Nettekoven, M. ;

Plancher, J. -M. ;

Raab, S. ;

Roche, O. ;

Schuler, F. ;

Taylor, S. ;

Ullmer, C. ;

Wiegand, R. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (19) :5713-5717

[10] A short history of SHELX [J].

Sheldrick, George M. .

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122

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