Reactivity of the -C(Cl)=C-C=N- moiety towards AlCl3-induced C-C bond forming reactions: a new synthesis of 7-(hetero)aryl-substituted pyrazolo[1,5-a]pyrimidines

被引：17

作者：

Kodimuthali, Arumugam ^{[1
]}

Nishad, T. C.

Prasunamba, Padala Lakshmi ^{[1
]}

Pal, Manojit

机构：

[1] Osmania Univ, Dept Chem, Univ Coll Sci, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 03期

关键词：

CHLORIDE-INDUCED HETEROARYLATION; INHIBITORS; PYRAZOLO<1,5-A>PYRIMIDINES; HETEROARENES; DERIVATIVES; PYRIMIDINE; AGENTS; ARENES;

D O I：

10.1016/j.tetlet.2008.11.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of the -C(Cl)=C-C=N- moiety towards an AlCl3-induced C-C bond forming reaction was investigated through the reaction of 7-chloro-5-phenyl-pyrazolo[1,5-a]pyrimidine with arenes and heteroarenes. This study furnished a novel and highly selective methodology for the preparation of 7-(hetero)aryl substituted-pyrazolopyrimidines in good to excellent yields under mild reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：354 / 358

页数：5

共 26 条

[11] SYNTHESIS OF SUBSTITUTED 5-AMINO-8-PHENYL-3H,6H-1,4,5A,8A-TETRAAZAACENAPHTHALEN-3-ONES, A NEW CLASS OF AGENTS FOR THE IMPROVEMENT OF COGNITION [J].

LEVIN, JI ;

EPSTEIN, JW ;

BEER, B ;

DEAN, WD ;

DUSZA, JP ;

TSENG, SS ;

SCHWEITZER, HJ ;

FRANCISCO, GD ;

CAIN, WT ;

BARTUS, RT ;

DEAN, RL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (09) :435-440

[12] Synthesis of pyrazolo[1,5-a]-, 1,2,4-triazolo[1,5-a]- and imidazo[1,2-a]pyrimidines related to zaleplon, a new drug for the treatment of insomnia [J].

Mustazza, C ;

Del Giudice, MR ;

Borioni, A ;

Gatta, F .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (05) :1119-1129

[13] 3-SUBSTITUTED 5,7-DIMETHYLPYRAZOLO[1,5-A]PYRIMIDINES, 3',5'-CYCLIC-AMP PHOSPHODIESTERASE INHIBITORS .1. [J].

NOVINSON, T ;

HANSON, R ;

DIMMITT, MK ;

SIMON, LN ;

ROBINS, RK ;

OBRIEN, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (06) :645-648

[14] NOVEL HETEROCYCLIC NITROFURFURAL HYDRAZONES - INVIVO ANTI-TRYPANOSOMAL ACTIVITY [J].

NOVINSON, T ;

BHOOSHAN, B ;

OKABE, T ;

REVANKAR, GR ;

ROBINS, RK ;

SENGA, K ;

WILSON, HR .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (04) :512-516

[15] A new synthesis of 2-substituted pyridines via aluminum chloride induced heteroarylation of arenes and heteroarenes [J].

Pal, M ;

Batchu, VR ;

Dager, I ;

Swamy, NK ;

Padakanti, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2376-2379

[16] Aluminum chloride-induced heteroarylation of arenes and heteroarenes.: 2.: A new synthesis of 4-substituted phthalazin-1(2H)-ones [J].

Pal, M ;

Batchu, VR ;

Parasuraman, K ;

Yeleswarapu, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6806-6809

[17] Regioselective aluminium chloride induced heteroarylation of pyrrolo[1,2-b]pyridazines:: its scope and application [J].

Pal, M ;

Batchu, VR ;

Khanna, S ;

Yeleswarapu, KR .

TETRAHEDRON, 2002, 58 (50) :9933-9940

[18]

PAL M, 2006, Patent No. 20060582012

[19]

PAL M, 2006, Patent No. 200601287291

[20] 2-arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides.: New potent and selective peripheral benzodiazepine receptor ligands [J].

Selleri, S ;

Bruni, F ;

Costagli, C ;

Costanzo, A ;

Guerrini, G ;

Ciciani, G ;

Costa, B ;

Martini, C .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (10) :2661-2671

← 1 2 3 →