Propanal in the syntheses of alkyl-substituted 3-cyano-2-piperidone, 3-cyano-2,5,6,7-tetrahydropyrindin-2(1H)-one, and 3-cyanopyridine-2(1H)-thione

被引:0
作者
Dyachenko V.D. [1 ]
Chernega A.N. [2 ]
机构
[1] Taras Shevchenko National Pedagogical University
[2] Organic Chemistry Institute, Ukraine National Academy of Sciences
关键词
3-cyano-4-ethyl-2,5,6,7-tetrahydropyrindin-2(1H)-one; 3-cyano-4-ethyl-5,6-hexamethylenepyridine-2(1H)-thione; Condensation; Cyanoacetamide; Cyanothioacetamide; Enamines; Michael adduct; Propanal; Thieno[2,3-b]pyridine;
D O I
10.1007/s10593-005-0244-y
中图分类号
学科分类号
摘要
Condensation of propanal with cyanothioacetamide and morpholine gave 3-cyano-4-ethyl-5-methyl-6-morpholino-2-piperidone, the structure of which was studied by X-ray analysis. Reaction of propanal with cyanothioacetamides and cycloalkanone enamines gave 3-cyano-4-ethyl-2,5,6,7-tetrahydropyrindin-2(1H)-one and 3-cyano-4-ethyl-5,6-hexamethylenepyridine-2(1H)-thione. The latter was used for the preparation of substituted 2-benzyloxycarbonylmethylthiopyridine and 3-amino-2-benzyloxycarbonylthieno[2,3-b]pyridine. ©2005 Springer Science+Business Media, Inc.
引用
收藏
页码:890 / 895
页数:5
相关论文
共 50 条
[21]   Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction [J].
Chitra, S. ;
Pandiarajan, K. .
TETRAHEDRON LETTERS, 2009, 50 (19) :2222-2224
[22]   Reaction of 3-Hydrazinylquinoxaline-2(1H)-one with 2-Hydroxyimino-1,3-dicarbonyl Compounds [J].
Bobrov, P. S. ;
Semichenko, E. S. ;
Kondrasenko, A. A. ;
Suboch, G. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (11) :1628-1636
[23]   Reaction of 3-Hydrazinylquinoxaline-2(1H)-one with 2-Hydroxyimino-1,3-dicarbonyl Compounds [J].
P. S. Bobrov ;
E. S. Semichenko ;
A. A. Kondrasenko ;
G. A. Suboch .
Russian Journal of Organic Chemistry, 2022, 58 :1628-1636
[24]   Preparation of 5-Cyano-4,6-dimethyl-2H-pyran-2-one and 3-Cyano-5-methoxy-4-methyl-5H-furan-2-one via a One-Pot, Domino-Knoevenagel process [J].
Dawadi, Prativa B. S. ;
Lugtenburg, Johan .
SYNTHETIC COMMUNICATIONS, 2010, 40 (17) :2539-2546
[25]   SYNTHESIS OF DERIVATIVES OF 5-(4,5-DIHYDRO-1H-3-PYRAZOLYL)-3,4-DIHYDRO-2(1H)-PYRIMIDONE [J].
Kolosov, M. A. ;
Orlov, V. D. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) :873-875
[26]   Synthesis of derivatives of 5-(4,5-dihydro-1H-3-pyrazolyl)-3,4-dihydro-2(1H)-pyrimidone [J].
M. A. Kolosov ;
V. D. Orlov .
Chemistry of Heterocyclic Compounds, 2009, 45 :873-875
[27]   Base-mediated one-pot synthesis of 3,4,5,6-tetrahydro-4-substituted benzo[h] quinazoline-2(1H)-thione derivatives and evaluation of their antioxidant activity [J].
Sivakumar, Matam ;
Prabakaran, Kaliyan ;
Perumal, Muthu Seenivasa .
SYNTHETIC COMMUNICATIONS, 2018, 48 (02) :197-207
[28]   Cerium (IV) Ammonium Nitrate as an Efficient Lewis Acid for the One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Their Corresponding 2-(1H) Thiones [J].
Sadek, Kamal Usef ;
Al-Qalaf, Fawzia ;
Abdelkhalik, Mervat Mohammed ;
Elnagdi, Mohamed Hilmy .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (02) :284-286
[29]   Environmentally Friendly Preparation of 3,4-Dihydropyrimidin-2(1H)-thiones Catalyzed by Al(H2PO4)3 [J].
Shaterian, Hamid Reza ;
Hosseinian, Asghar ;
Ghashang, Majid .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (01) :126-134
[30]   Efficient One-Pot Synthesis of 4-Aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]pyridin-2-one and 4-Aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-one Derivatives Under Solvent-Free Conditions [J].
Rong, Liangce ;
Han, HongXia ;
Jiang, Hong ;
Zhang, Qiya ;
Tu, Shuajiang .
SYNTHETIC COMMUNICATIONS, 2009, 39 (06) :1027-1034