Synthesis of 7-[2-(Dimethylamino)vinyl]pyrazolo[1,5-a]pyrimidine-6-carbonitriles and Their Heterocyclizations with N1 Synthons

被引:0
作者
Polikarchuk, V. A. [1 ]
Derkachev, M. S. [1 ]
Shikhaliev, Kh. S. [1 ]
机构
[1] Voronezh State Univ, Voronezh 394006, Russia
关键词
pyrazolo[1,5-a]pyrimidine; 3-oxobutanenitrile; heterocyclization; N1; synthon; dimethylaminovinyl derivative; annulation; pyrazolo[1,5-a]pyrido[3,4-e]pyrimidine; EFFICIENT SYNTHESIS; DERIVATIVES; ENAMINONITRILES; RING; PYRIMIDINE; REACTIVITY; PYRAZOLE; FACILE;
D O I
10.1134/S1070428024050087
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of new 7-methylazolo[1,5-a]pyrimidine-6-carbonitriles for the construction of heterocyclic systems annulated at the pyrimidine ring has been demonstrated. Cascade cyclizations are carried out via the intermediate dimethylaminovinyl derivatives. The specific features of the cascade reactions with ammonia or aliphatic amines as N1 synthons, depending on the reaction conditions, are demonstrated.
引用
收藏
页码:852 / 861
页数:10
相关论文
共 42 条
[1]   Studies using (E)-6-oxo-1-aryl-4-(2-N-piperidinyl)vinyl-1,6-dihydropyridazine-5-carbonitrile [J].
Abdelhamid, Ismail Abdelshafy ;
Ghozlan, Said Ahmed Soliman ;
Kolshorn, Heinz ;
Meier, Herbert ;
Elnagdi, Mohamed Hilmy .
HETEROCYCLES, 2007, 71 (12) :2627-2637
[2]   Heterocyclic synthesis via enaminonitriles:: An efficient, one step synthesis of some novel azolo[1,5-a]pyrimidine, pyrimido[1,2-a]-benzimidazole, pyrido[1,2-a]benzimidazole pyrimidine and pyrazole derivatives [J].
Al-Afaleq, EI .
SYNTHETIC COMMUNICATIONS, 2000, 30 (11) :1985-1999
[3]   Disperse Dyes Based on Aminothiophenes: Their Dyeing Applications on Polyester Fabrics and Their Antimicrobial Activity [J].
Al-Mousawi, Saleh Mohammed ;
El-Apasery, Morsy Ahmed ;
Mahmoud, Huda M. .
MOLECULES, 2013, 18 (06) :7081-7092
[4]   Synthesis of new pyrazolo[1,5-α]pyrimidines and pyrazolo[3,4-b]pyridines [J].
Al-Mousawi, SM ;
Mohammad, MA ;
Elnagdi, MH .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) :989-991
[5]   Synthesis of new azoloazine derivatives:: New routes to 1,2,4-triazolo[4,3-a] pyrimidines, pyrazolo[1,5a]pyridines and pyrazolo[3,4-b]pyridinones [J].
Al-Saleh, B ;
Abdel-Khalik, MM ;
Al-Enzy, A ;
Elnagdi, MH .
JOURNAL OF CHEMICAL RESEARCH-S, 1999, (11) :654-655A
[6]  
Al-Zaydi KM, 2000, J CHEM RES, P13
[7]   Facile Iterative Synthesis of 2,5-Terpyrimidinylenes as Nonpeptidic α-Helical Mimics [J].
Anderson, Laura ;
Zhou, Mingzhou ;
Sharma, Vasudha ;
McLaughlin, Jillian M. ;
Santiago, Daniel N. ;
Fronczek, Frank R. ;
Guida, Wayne C. ;
McLaughlin, Mark L. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :4288-4291
[8]   Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo [1,5-a]pyrimidines as novel larotrectinib analogs [J].
Attia, Mohamed H. ;
Elrazaz, Eman Z. ;
El-Emam, Soad Z. ;
Taher, Azza T. ;
Abdel-Aziz, Hatem A. ;
Abouzid, Khaled A. M. .
BIOORGANIC CHEMISTRY, 2020, 94
[9]  
Brough S. J., 2010, WO Patent Appl., Patent No. [WO2010/039079, 2010039079]
[10]   REACTIONS OF 2,2-DIALKYL-1,2-DIHYDROQUINOLINES .2. BROMO-DERIVATIVES OF 1,2-DIHYDRO-2,2,4-TRIMETHYLQUINOLINE [J].
BROWN, JP ;
JACKMAN, LM .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP) :3132-&