Catalyst-free tandem Michael addition-cyclization reactions in aqueous media for the synthesis of benzimidazo[1,2-a]pyrimidinone derivatives

被引：2

作者：

Ren ChuanLi ^{[1
]}

Wang Yan ^{[1
]}

Wang Dong ^{[1
]}

Chen YongJun ^{[1
]}

Liu Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2010年 / 53卷 / 07期

基金：

中国国家自然科学基金;

关键词：

aqueous media; Baylis-Hillman alcohol; 2-aminobenzimidazole; pesticidal activity; BAYLIS-HILLMAN REACTION; RATE ACCELERATION; WATER; ALKYLATION; EFFICIENT; ACID;

D O I：

10.1007/s11426-010-4033-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalyst-free reactions of Baylis-Hillman alcohols (1a-i) with 2-aminobenzimidazole (2) in THF-H(2)O (1:4) were developed for the convenient and greener synthesis of benzimidazo[1,2-a]pyrimidinone derivatives (3a-i). The pesticidal activities of 3a-i were examined to investigate a new biological activity of the imidazo[1,2-a]pyrimidinone-type compounds.

引用

页码：1492 / 1496

页数：5

共 26 条

[1]

ASOBO PF, 2001, J CHEM SOC P1

[2] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[3] The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Raju Jannapu .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588

[4] Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water [J].

Cai, JX ;

Zhou, ZH ;

Zhao, GF ;

Tang, CC .

ORGANIC LETTERS, 2002, 4 (26) :4723-4725

[5]

Chakraborti AK, 2007, GREEN CHEM, V9, P1335, DOI 10.1039/b710414f

[6] Synthesis of pyrimido[1,2-α]benzimidazol-4(10H)-one derivatives and evaluation of their interactions with DNA [J].

Da Settimo, A ;

Primofiore, G ;

Da Settimo, F ;

Marini, AM ;

Taliani, S ;

Salerno, S ;

Via, LD .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (06) :1091-1096

[7]

DESCOURS D, 1983, SYNTHESIS-STUTTGART, P1033

[8] Rhodium-catalyzed reactions of arylbismuth and aryllead reagents with a chiral glyoxylate hydrate in air and water: water-promoted diastereoselectivity enhancement [J].

Ding, R ;

Ge, CS ;

Chen, YJ ;

Wang, D ;

Li, CJ .

TETRAHEDRON LETTERS, 2002, 43 (43) :7789-7791

[9]

GRIECO A, 1998, ORGANIC SYNTHESIS WA

[10] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 2-SUBSTITUTED AND 3-SUBSTITUTED IMIDAZO[1,2-ALPHA]PYRIMIDINE [J].

GUEIFFIER, A ;

BLACHE, Y ;

CHAPAT, JP ;

ELHAKMAOUI, A ;

ESSASSI, EM ;

ANDREI, G ;

SNOECK, R ;

DECLERCQ, E ;

CHAVIGNON, O ;

TEULADE, JC ;

FAUVELLE, F .

NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5) :551-554

← 1 2 3 →