Efficient Synthesis of New Tetracyclic Benzofuro[3,2-d]imidazo[1,2-a]pyrimidine-2,5-(1H,3H)-diones

被引：3

作者：

Hu Yanggen ^{[1
,2
,3
]}

Liu Min ^{[1
]}

Ding Mingwu ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China

[2] Yunyang Med Coll, Taihe Hosp, Dept Pharm, Shiyan 442000, Hubei, Peoples R China

[3] Yunyang Med Coll, Inst Med Chem, Shiyan 442000, Hubei, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2010年 / 28卷 / 02期

基金：

中国国家自然科学基金;

关键词：

benzofuro[3,2-d]imidazo[1,2-a]pyrimidine-2,5-(1H,3H)-dione; iminophosphorane; aza-Wittig reaction; isocyanate; carbodiimide; WITTIG/HETEROCUMULENE-MEDIATED ANNULATION; FUNGICIDAL ACTIVITIES; IMIDAZOLE ALKALOIDS; BIOLOGICAL-ACTIVITY; DERIVATIVES;

D O I：

10.1002/cjoc.201090072

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The aza-Wittig reaction of iminophosphorane (1) with aromaic isocyanates gave carbodiimides (2), which were allowed to react further with a-amino ester in the presence of a catalytic amount of sodium ethoxide to give selectively new tetracyclic benzofuro [3,2-d]imidazo[1,2-a]pyrimidine-2,5-(1H,3H)-diones (5) in good yields. X-ray structure analysis of 5i verified the proposed structure and the reaction selectivity.

引用

页码：309 / 312

页数：4

共 21 条

[1]

Bascou J. P., 1999, Patent No. [US6002016, 6002016]

[2]

Bodke Y, 2003, J INDIAN CHEM SOC, V80, P187

[3] NEW LEUKOTRIENE-B4 RECEPTOR ANTAGONIST - LEUCETTAMINE-A AND RELATED IMIDAZOLE ALKALOIDS FROM THE MARINE SPONGE LEUCETTA-MICRORAPHIS [J].

CHAN, GW ;

MONG, S ;

HEMLING, ME ;

FREYER, AJ ;

OFFEN, PH ;

DEBROSSE, CW ;

SARAU, HM ;

WESTLEY, JW .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01) :116-121

[4] Synthesis and fungicidal activities of derivatives of 2-alkylthio-3-amino-4H-imidazol-4-one [J].

Ding, MW ;

Chen, YF ;

Huang, NY .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (11) :2287-2296

[5]

FARAG EAE, 2008, CHINESE J CHEM, V26, P1509

[6]

Fu BQ, 2007, CHINESE J ORG CHEM, V27, P1268

[7] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SPIROCYCLIC BENZOPYRAN IMIDAZOLONE POTASSIUM CHANNEL OPENERS [J].

GADWOOD, RC ;

KAMDAR, BV ;

DUBRAY, LAC ;

WOLFE, ML ;

SMITH, MP ;

WATT, W ;

MIZSAK, SA ;

GROPPI, VE .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) :1480-1487

[8]

Glazer E.A., 1988, [No title captured], Patent No. [US 4725599, 4725599]

[9] Efficient iminophosphorane-mediated preparation of benzofuro-[3,2-d]pyrimidin-4(3H)-ones and unexpected ring opening products [J].

Hu, Yang-Gen ;

Liu, Ming-Guo ;

Ding, Ming-Wu .

HELVETICA CHIMICA ACTA, 2008, 91 (05) :862-872

[10] Synthesis of new tetracyclic benzo[4,5]furo[3,2-d]-1,2,4-triazolo [1,5-a]pyrimidin-5(1H)-ones via a tandem aza-Wittig/Heterocumulene-mediated annulation [J].

Hu, Yang-Gen ;

Yang, Sheng-Jun ;

Ding, Ming-Wu .

ARKIVOC, 2008, :297-306

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