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
[1]   Isothiazole and isoxazole fused pyrimidones as PDE7 inhibitors: SAR and pharmacokinetic evaluation [J].
Banerjee, Abhisek ;
Yadav, Pravin S. ;
Bajpai, Malini ;
Sangana, Ramachandra Rao ;
Gullapalli, Srinivas ;
Gudi, Girish S. ;
Gharat, Laxmikant A. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (09) :3223-3228
[2]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[3]   Advances and adventures in amination reactions of olefins and alkynes [J].
Beller, M ;
Breindl, C ;
Eichberger, M ;
Hartung, CG ;
Seayad, J ;
Thiel, OR ;
Tillack, A ;
Trauthwein, H .
SYNLETT, 2002, (10) :1579-1594
[4]   TOTAL SYNTHESIS AND EVALUATION OF (+/-)-N-(TERT-BUTYLOXYCARBONYL)-CBI, (+/-)-CBI-CDPI1, AND (+/-)-CBI-CDPI2 - CC-1065 FUNCTIONAL AGENTS INCORPORATING THE EQUIVALENT 1,2,9,9A-TETRAHYDROCYCLOPROP[1,2-C]BENZ[1,2-E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].
BOGER, DL ;
ISHIZAKI, T ;
WYSOCKI, RJ ;
MUNK, SA ;
KITOS, PA ;
SUNTORNWAT, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6461-6463
[5]   Asymmetric Hydrogenation of Cyclic Imines and Enamines: Access to 1,5-Benzodiazepine Pharmacophores [J].
Borrmann, Ruediger ;
Koenigs, Rene M. ;
Zoller, Jochen ;
Rueping, Magnus .
SYNTHESIS-STUTTGART, 2017, 49 (02) :310-318
[6]   Aminovinyl ketones and aminovinyl esters as C-C-N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines [J].
Charushin, VN ;
Mochulskaya, NN ;
Andreiko, AA ;
Filyakova, VI ;
Kodess, MI ;
Chupakhin, ON .
TETRAHEDRON LETTERS, 2003, 44 (11) :2421-2424
[7]   Non-steroidal anti-inflammatory agents. Part 23 - Synthesis and pharmacological activity of enaminones which inhibit both bovine cyclooxygenase and 5-lipoxygenase [J].
Dannhardt, G ;
Bauer, A ;
Nowe, U .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (03) :256-263
[8]   Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].
Dehli, JR ;
Legros, J ;
Bolm, C .
CHEMICAL COMMUNICATIONS, 2005, (08) :973-986
[9]   Synthesis and anticonvulsant activity of enaminones Part 7. Synthesis and anticonvulsant evaluation of ethyl 4-[(substituted phenyl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylates and their corresponding 5-methylcyclohex-2-enone derivatives [J].
Eddington, ND ;
Cox, DS ;
Khurana, M ;
Salama, NN ;
Stables, JP ;
Harrison, SJ ;
Negussie, A ;
Taylor, RS ;
Tran, UQ ;
Moore, JA ;
Barrow, JC ;
Scott, KR .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (01) :49-64
[10]   FORMATION AND STRUCTURE OF STABLE, ISOLABLE CONJUGATED PRIMARY ENAMINES [J].
ERKER, G ;
PFAFF, R ;
KOWALSKI, D ;
WURTHWEIN, EU ;
KRUGER, C ;
GODDARD, R .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6771-6778