Synthesis of pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives via Aza-Diels-Alder reaction: evaluation of torsion effect of pyrazoylimines

被引：10

作者：

Wang, Li-Ya ^{[1
]}

Uramaru, Naoto ^{[2
]}

Wong, Fung Fuh ^{[3
,4
]}

机构：

[1] China Med Univ, PhD Program Canc Biol & Drug Discovery, Taichung 40402, Taiwan

[2] Nihon Pharmaceut Univ, Dept Environm Sci, Ina, Saitama, Japan

[3] China Med Univ, Sch Pharm, Taichung 40402, Taiwan

[4] China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan

来源：

TETRAHEDRON | 2014年 / 70卷 / 41期

关键词：

Pyrazolopyrrolopyridines; Aza-Diels-Alder reaction; Pyrazoylimines; Leaving group effect;

D O I：

10.1016/j.tet.2014.08.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modified method for the synthesis of pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine was developed through an Aza-Diels-Alder reaction of pyrazoylimines with maleimides in the sealed tube. Based on the control experiment, the yields for the Aza-Diels-Alder reaction seemed proportional to the suitable torsion conformation of pyrazoylimine, which was modulated by N,N-disubstituted amidinyl moiety. The versatile sealed tube technique was also proved to promote the higher isolated yields in the Aza-Diels-Alder reaction. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7439 / 7444

页数：6

共 15 条

[1] Enantioselective Diels-Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amine [J].

Bai, Jian-Fei ;

Guo, Yun-Long ;

Peng, Lin ;

Jia, Li-Na ;

Xu, Xiao-Ying ;

Wang, Li-Xin .

TETRAHEDRON, 2013, 69 (03) :1229-1233

[2]

Draz-Ortiz A., 2000, TETRAHEDRON, V55, P1569

[3]

Hardman J.G., 2001, GOODMAN GILMANS PHAR

[4] Sodium bis(trimethylsilyl)amide and lithium diisopropylamide in deprotection of alkyl aryl ethers: alpha-effect of silicon [J].

Hwu, JR ;

Wong, FF ;

Huang, JJ ;

Tsay, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4097-4104

[5] Analgesia and hyperalgesia from GABA-mediated modulation of the cerebral cortex [J].

Jasmin, L ;

Rabkin, SD ;

Granato, A ;

Boudah, A ;

Ohara, PT .

NATURE, 2003, 424 (6946) :316-320

[6] Synthesis of fused pyridopyrrolidine dione derivatives using hetero Diels-Alder reactions [J].

Mason, HJ ;

Wu, XM ;

Schmitt, R ;

Macor, JE ;

Yu, GX .

TETRAHEDRON LETTERS, 2001, 42 (51) :8931-8934

[7] Sedation and antinociception induced by a new pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivative (LASSBio-873) is modulated by activation of muscarinic receptors [J].

Mendes, Thaiana C. F. ;

Raimundo, Juliana M. ;

Nascimento-Junior, Nailton M. ;

Fraga, Carlos A. M. ;

Barreiro, Eliezer J. ;

Sudo, Roberto T. ;

Zapata-Sudo, Gisele .

PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 2009, 94 (01) :72-74

[8] Design, synthesis, and pharmacological evaluation of new neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives with in vivo hypnotic and analgesic profile [J].

Menegatti, R ;

Silva, GMS ;

Zapata-Sudo, G ;

Raimundo, JM ;

Sudo, RT ;

Barreiro, EJ ;

Fraga, CAM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (03) :632-640

[9]

Mohler H, 2001, Curr Opin Pharmacol, V1, P22, DOI 10.1016/S1471-4892(01)00008-X

[10] Microwave-assisted synthesis and structure-activity relationships of neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives [J].

Nascimento-Junior, Nailton M. ;

Mendes, Thaiana C. F. ;

Leal, Daniella M. ;

Correa, Claudia Maria N. ;

Sudo, Roberto T. ;

Zapata-Sudo, Gisele ;

Barreiro, Eliezer J. ;

Fraga, Carlos A. M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) :74-77

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