Efficient Route for Synthesis of Enamines from 1,3-Alkyl-2-Thioxodihydropyrimidine-4,6(1H,5H)-dione Enols

被引:0
作者
Sharma, Anamika [1 ,2 ]
Almarhoon, Zainab M. [3 ]
El-Faham, Ayman [3 ,4 ]
de la Torre, Beatriz G. [5 ]
Albericio, Fernando [2 ,3 ,6 ,7 ]
机构
[1] Univ KwaZulu Natal, Coll Hlth Sci, Sch Hlth Sci, Univ Rd, ZA-4000 Durban, South Africa
[2] Univ KwaZulu Natal, Sch Chem & Phys, Private Bag X54001,Westville Campus, ZA-4000 Durban, South Africa
[3] King Saud Univ, Dept Chem, Coll Sci, Riyadh 11451, Saudi Arabia
[4] Alexandria Univ, Dept Chem, Fac Sci, Alexandria 21321, Egypt
[5] Univ KwaZulu Natal, Coll Hlth Sci, KRISP, ZA-4001 Durban, South Africa
[6] Univ Barcelona, Dept Organ Chem, Marti i Franques 1-11, E-08028 Barcelona, Spain
[7] Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona Sci Pk,Baldiri Reixac 10, Barcelona 08028, Spain
基金
新加坡国家研究基金会;
关键词
Thiobarbituric acid; enols; enamines; greener approach; ammonium chloride; HPLC; HYDROGENATION; INHIBITORS; AGENTS;
D O I
10.2174/1570178616666190409145118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we report a greener approach for the synthesis of enamines from enols of 1,3-alkyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (thiobarbituric acid) acid using ammonium chloride and ethanol as solvents. This protocol removes the need for catalysts or harsh conditions.
引用
收藏
页码:538 / 540
页数:3
相关论文
共 25 条
[11]   A remarkably rapid regioselective synthesis of β-enaminones using silica chloride in a heterogeneous as well as an ionic liquid in a homogeneous medium at room temperature [J].
Gholap, AR ;
Chakor, NS ;
Daniel, T ;
Lahoti, RJ ;
Srinivasan, KV .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 245 (1-2) :37-46
[12]   Isothiazolopyrimidines and isoxazolopyrimidines as novel multi-targeted inhibitors of receptor tyrosine kinases [J].
Ji, Zhiqin ;
Ahmed, Asma A. ;
Albert, Daniel H. ;
Bouska, Jennifer J. ;
Bousquet, Peter F. ;
Cunha, George A. ;
Glaser, Keith B. ;
Guo, Jun ;
Li, Junling ;
Marcotte, Patrick A. ;
Moskey, Maria D. ;
Pease, Lori J. ;
Stewart, Kent D. ;
Yates, Melinda ;
Davidsen, Steven K. ;
Michaelides, Michael R. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (16) :4326-4330
[13]   Structure - Nucleophilicity relationships for enamines [J].
Kempf, B ;
Hampel, N ;
Ofial, AR ;
Mayr, H .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (10) :2209-2218
[14]   METHYLENATIONS OF HETEROATOM-SUBSTITUTED CARBONYLS WITH DIMETHYL TITANOCENE [J].
PETASIS, NA ;
LU, SP .
TETRAHEDRON LETTERS, 1995, 36 (14) :2393-2396
[15]   REACTIONS OF STANNIC AMINES WITH CARBONYL DERIVATIVES [J].
POMMIER, JC ;
ROUBINEA.A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 50 (01) :101-111
[16]   An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template [J].
Savarin, CG ;
Murry, JA ;
Dormer, PG .
ORGANIC LETTERS, 2002, 4 (12) :2071-2074
[17]   Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity [J].
Sharma, Anamika ;
Noki, Sikabwe ;
Zamisa, Sizwe J. ;
Hazzah, Heba A. ;
Almarhoon, Zainab M. ;
El-Faham, Ayman ;
de la Torre, Beatriz G. ;
Albericio, Fernando .
CHEMMEDCHEM, 2018, 13 (18) :1923-1930
[18]   ENAMINE ALKYLATION AND ACYLATION OF CARBONYL COMPOUNDS [J].
STORK, G ;
SZMUSZKOVICZ, J ;
TERRELL, R ;
BRIZZOLARA, A ;
LANDESMAN, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :207-&
[19]  
TAGUCHI K, 1971, J ORG CHEM, V36, P1570
[20]   Solvent-free organic synthesis [J].
Tanaka, K ;
Toda, F .
CHEMICAL REVIEWS, 2000, 100 (03) :1025-1074