Microwave-assisted synthesis of pyrimidine libraries

被引：88

作者：

Bagley, MC ^{[1
]}

Hughes, DD ^{[1
]}

Lubinu, MC ^{[1
]}

Merritt, EA ^{[1
]}

Taylor, PH ^{[1
]}

Tomkinson, NCO ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

QSAR & COMBINATORIAL SCIENCE | 2004年 / 23卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

pyrimidines; microwave synthesis; heterocycles; library synthesis;

D O I：

10.1002/qsar.200420044

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Di- or trisubstituted pyrimidine libraries are prepared in good yield by the microwave irradiation of an alkynone and either an amidine or guanidine at 120-150degreesC in acetonitrile in the presence of sodium carbonate or at 100degreesC after treatment with methanolic sodium methoxide in a sealed tube using a monomodal microwave synthesiser. These rapid and efficient methods often require no chromatographic purification and so are appropriate for automated combinatorial methodology and have been applied in the synthesis of a small library of potentially, useful novel ligands for the estrogen receptor based on the pyrimidine template.

引用

页码：859 / 867

页数：9

共 49 条

[1] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ ;

Tang, LT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2311-2316

[2] The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :855-866

[3]

ALTALIB M, 1992, SYNTHESIS-STUTTGART, P875

[4] ACETYLINIC KETONES .2. REACTION OF ACETYLENIC KETONES WITH NUCLEOPHILIC NITROGEN-COMPOUNDS [J].

BADDAR, FG ;

ALHAJJAR, FH ;

ELRAYYES, NR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (02) :257-268

[5] New N-halosuccinimide-mediated reactions for the synthesis of pyridines [J].

Bagley, MC ;

Glover, C ;

Merritt, EA ;

Xiong, X .

SYNLETT, 2004, (05) :811-814

[6] Highly efficient synthesis of pyrimidines under microwave-assisted conditions [J].

Bagley, MC ;

Hughes, DD ;

Taylor, PH .

SYNLETT, 2003, (02) :259-261

[7] A facile solution phase combinatorial synthesis of tetrasubstituted pyridines using the Bohlmann-Rahtz heteroannulation reaction [J].

Bagley, MC ;

Dale, JW ;

Ohnesorge, M ;

Xiong, X ;

Bower, J .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (01) :41-44

[8] A new one-step synthesis of pyridines under microwave-assisted conditions [J].

Bagley, MC ;

Lunn, R ;

Xiong, X .

TETRAHEDRON LETTERS, 2002, 43 (46) :8331-8334

[9] Microwave-assisted synthesis of 5-deaza-5,8-dihydropterins [J].

Bagley, MC ;

Singh, N .

SYNLETT, 2002, (10) :1718-1720

[10] Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction [J].

Bagley, MC ;

Brace, C ;

Dale, JW ;

Ohnesorge, M ;

Phillips, NG ;

Xiong, X ;

Bower, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14) :1663-1671

← 1 2 3 4 5 →