High-throughput preparation of alkyl 4-aryl substituted-2-methyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylates under microwave irradiation

被引：5
|
作者：
Rodriguez, Hortensia [1 ,2 ]
Coro, Julieta [1 ]
Lam, Anabel [3 ]
Salfran, Esperanza [1 ]
Rodriguez-Salarichs, Javier [3 ]
Suarez, Margarita [1 ]
Albericio, Fernando [2 ,4 ,5 ]
Martin, Nazario [6 ]
机构：
[1] Univ La Habana, Fac Quim, Dept Quim Organ, Lab Sintesis Organ, Havana 10400, Cuba
[2] Inst Res Biomed, Barcelona 08028, Spain
[3] Univ Havana, Inst Mat Sci & Technol IMRE, Zeolite Engn Lab, Havana 10400, Cuba
[4] CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, Barcelona 08028, Spain
[5] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
[6] Univ Complutense, Fac Ciencias Quim, Dept Quim Inorgan, E-28040 Madrid, Spain
来源：
ARKIVOC | 2011年
关键词：
Microwave irradiation; Lawesson's reagent; thiopyridones; theoretical calculation; heterocycles; ONE-POT SYNTHESIS; ORGANIC-SYNTHESIS; LAWESSONS REAGENT; TETRATHIAFULVALENE; COMBINATORIAL; DERIVATIVES; THIONATION; OVENS;
D O I：
10.3998/ark.5550190.0012.909
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient high-throughput synthesis of 4-aryl substituted 1,4,5,6-tetrahydro-2-methyl-6-thioxopyridine-3-carboxylates 5a-p was developed by using Lawesson's reagent, a very effective thionating reagent for carbonyl compounds, under conventional conditions and microwave irradiation, In order to gain a better understanding of the structure of the heterocycles obtained, theoretical calculations at the ab initio level were carried out
引用
收藏
页码：125 / +
页数：23
相关论文
共 50 条
  • [1] Synthesis and Heterocyclization of 1-Aryl-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylates
    Sapijanskaite, Birute
    Mickeviciene, Kristina
    Kantminiene, Kristina
    Belyakov, Sergey
    Mickevicius, Vytautas
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (05) : 2605 - 2613
  • [2] PREPARATION OF CHIRAL β-ENAMINO ESTERS FROM METHYL PROPIOLATE: SYNTHESIS OF CHIRAL METHYL 1-SUBSTITUTED 6-OXO-1,4,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATES
    Pilotzi, Hugo
    Gnecco, Dino
    Orea, Maria L.
    Juarez, Jorge R.
    Aparicio, David M.
    Teran, Joel L.
    HETEROCYCLES, 2018, 96 (05) : 899 - 905
  • [3] Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates
    A. N. Vereshchagin
    K. A. Karpenko
    T. M. Iliyasov
    M. N. Elinson
    E. O. Dorofeeva
    A. N. Fakhrutdinov
    M. P. Egorov
    Russian Chemical Bulletin, 2018, 67 : 2049 - 2053
  • [4] Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates
    Vereshchagin, A. N.
    Karpenko, K. A.
    Iliyasov, T. M.
    Elinson, M. N.
    Dorofeeva, E. O.
    Fakhrutdinov, A. N.
    Egorov, M. P.
    RUSSIAN CHEMICAL BULLETIN, 2018, 67 (11) : 2049 - 2053
  • [5] Solvent-free synthesis of 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones under microwave irradiation
    Rodríguez, H
    Suarez, M
    Pérez, R
    Petit, A
    Loupy, A
    TETRAHEDRON LETTERS, 2003, 44 (18) : 3709 - 3712
  • [6] Synthesis and properties of 4,5-trans-4-aryl-3-cyano-6-hydroxy-6-methyl-5-pyridinio-1,4,5,6-tetrahydropyridine-2-thiolates
    Krauze, A
    Duburs, G
    HETEROCYCLIC COMMUNICATIONS, 2000, 6 (03) : 265 - 270
  • [7] Multicomponent synthesis and antimicrobial activity of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxylates
    A. N. Yankin
    N. V. Nosova
    V. L. Gein
    M. V. Tomilov
    Russian Journal of General Chemistry, 2015, 85 : 844 - 850
  • [8] Synthesis of alkyl 4-aryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates
    V. L. Gein
    M. I. Kazantseva
    L. F. Gein
    P. A. Slepukhin
    Russian Journal of Organic Chemistry, 2014, 50 : 240 - 243
  • [9] Synthesis of alkyl 4-aryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates
    Gein, V. L.
    Kazantseva, M. I.
    Gein, L. F.
    Slepukhin, P. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (02) : 240 - 243
  • [10] Ethyl 5-ethoxymethylene-2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylate
    de Armas, HN
    Peeters, OM
    Blaton, NM
    De Ranter, CJ
    Navarro, MS
    Reyes, YV
    Rodríguez, EO
    Salfrán, E
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O230 - O231
12345