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

[1]

Abdel-Khalik MM, 2001, SYNTHESIS-STUTTGART, P1861

[2] Heterocyclic synthesis via enaminonitriles:: An efficient, one step synthesis of some novel azolo[1,5-a]pyrimidine, pyrimido[1,2-a]-benzimidazole, pyrido[1,2-a]benzimidazole pyrimidine and pyrazole derivatives [J].

Al-Afaleq, EI .

SYNTHETIC COMMUNICATIONS, 2000, 30 (11) :1985-1999

[3] Synthesis and SAR of a new series of COX-2-selective inhibitors:: Pyrazolo[1,5-α]pyrimidines [J].

Almansa, C ;

de Arriba, AF ;

Cavalcanti, FL ;

Gómez, LA ;

Miralles, A ;

Merlos, M ;

García-Rafanell, J ;

Forn, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) :350-361

[4]

Bondock S., 2008, EUR J MED CHEM, V20, P1

[5]

DUSZA JP, 1981, Patent No. 4281000

[6] SYNTHESIS OF SUBSTITUTED AZAINDENES - SYNTHESIS OF NEW PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES [J].

ELNAGDI, MH ;

ERIAN, AW .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (06) :1854-1856

[7] Optimization of a pyrazolo[1,5-a]pyrimidine class of KDR kinase inhibitors:: Improvements in physical properties enhance cellular activity and pharmacokinetics [J].

Fraley, ME ;

Rubino, RS ;

Hoffman, WF ;

Hambaugh, SR ;

Arrington, KL ;

Hungate, RW ;

Bilodeau, MT ;

Tebben, AJ ;

Rutledge, RZ ;

Kendall, RL ;

McFall, RC ;

Huckle, WR ;

Coll, KE ;

Thomas, KA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (24) :3537-3541

[8]

GUZI TJ, 2004, Patent No. 20040225601

[9] 3-HALO-5,7-DIMETHYLPYRAZOLO[1,5-A]PYRIMIDINES, A NON-BENZODIAZEPINOID CLASS OF ANTI-ANXIETY AGENTS DEVOID OF POTENTIATION OF CENTRAL NERVOUS-SYSTEM DEPRESSANT EFFECTS OF ETHANOL OR BARBITURATES [J].

KIRKPATRICK, WE ;

OKABE, T ;

HILLYARD, IW ;

ROBINS, RK ;

DREN, AT ;

NOVINSON, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (03) :386-393

[10] Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines [J].

Kiselyov, AS ;

Smith, L .

TETRAHEDRON LETTERS, 2006, 47 (15) :2611-2614

← 1 2 3 →