New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis-Hillman Adducts

被引：12

作者：

Zhong, Ying ^{[1
]}

Wu, Lei ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 19期

基金：

中国国家自然科学基金;

关键词：

azides; heterocycles; cyclizations; Wittig reactions; amines; alcohols; phenols; DERIVATIVES; ANTAGONISTS; CONSTRUCTION;

D O I：

10.1055/s-0032-1317034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azides obtained from Baylis-Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.

引用

页码：3085 / 3089

页数：5

共 27 条

[1] Domino reactions initiated by intramolecular hydride transfers from tri(di)arylmethane fragments to ketenimine and carbodiimide functions [J].

Alajarin, Mateo ;

Bonillo, Baltasar ;

Ortin, Maria-Mar ;

Sanchez-Andrada, Pilar ;

Vidal, Angel ;

Orenes, Raul-Angel .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4690-4700

[2] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[3] aza-Baylis-Hillman Reaction [J].

Declerck, Valerie ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMICAL REVIEWS, 2009, 109 (01) :1-48

[4] Facile Preparation of 3-Substituted Benzisothiazoles from o-Mercaptoacylphenones [J].

Devarie-Baez, Nelmi O. ;

Xian, Ming .

ORGANIC LETTERS, 2010, 12 (04) :752-754

[5] Application of bis(iminophosphorane) in heterocyclic synthesis:: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones [J].

Ding, MW ;

Xu, SZ ;

Zhao, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8366-8371

[6] Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists [J].

Dolman, NP ;

More, JCA ;

Alt, A ;

Knauss, JL ;

Troop, HM ;

Bleakman, D ;

Collingridge, GL ;

Jane, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (08) :2579-2592

[7] Synthesis and pharmacology of willardiine derivatives acting as antagonists of kainate receptors [J].

Dolman, NP ;

Troop, HM ;

More, JCA ;

Alt, A ;

Knauss, JL ;

Nistico, R ;

Jack, S ;

Morley, RM ;

Bortolotto, ZA ;

Roberts, PJ ;

Bleakman, D ;

Collingridge, GL ;

Jane, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (24) :7867-7881

[8] Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam [J].

Gichinga, Moses G. ;

Olson, Jeremy P. ;

Butala, Elizabeth ;

Navarro, Hernan A. ;

Gilmour, Brian P. ;

Mascarella, S. Wayne ;

Carroll, F. Ivy .

ACS MEDICINAL CHEMISTRY LETTERS, 2011, 2 (12) :882-884

[9] Synthesis of nitrogen bicyclic scaffolds: pyrimido[1,2-a]pyrimidine-2,6-diones [J].

Grosjean, Sylvain ;

Triki, Smail ;

Meslin, Jean-Claude ;

Julienne, Karine ;

Deniaud, David .

TETRAHEDRON, 2010, 66 (52) :9912-9924

[10] Efficient Regioselective Synthesis of Indole N-Carboximidamides and N-Carboximidoates by a Sequential Aza-Wittig/Ag(I)-Catalyzed Cyclization [J].

Huang, Nian-Yu ;

Liu, Ming-Guo ;

Ding, Ming-Wu .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) :6874-6877

← 1 2 3 →