Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines
The Biginelli-type reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds was studied in detail. We found that the reaction requires no catalysts and proceeds in boiling DMF to give 2-aryl-6-RC(O)-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carbonitriles in good yie...
Na minha lista:
| Главные авторы: | , |
|---|---|
| Formato: | Статья |
| Idioma: | English |
| Publicado em: |
Royal Society of Chemistry
2018
|
| Assuntos: | |
| Acesso em linha: | https://www.scopus.com/record/display.uri?eid=2-s2.0-84985023389&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=4deb6b7c4ec3f54375d585c101df8694&sot=afnl&sdt=sisr&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Catalyst-free+Biginelli-type+synthesis+of+new+functionalized+4%2c7-dihydropyrazolo%5b1%2c5-%3a+A%5d+pyrimidines%29&relpos=0&citeCnt=2&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/3429 |
| Tags: |
Adicionar Tag
Sem tags, seja o primeiro a adicionar uma tag!
|
| id |
ir-20.500.12258-3429 |
|---|---|
| record_format |
dspace |
| spelling |
ir-20.500.12258-34292020-07-31T10:04:51Z Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines Dotsenko, V. V. Доценко, В. В. Aldehyde derivative Carbene Carbonyl derivative Cyanide Cyclohexane derivative Pyrazolopyrimidine derivative Quinazoline derivative Synthesis The Biginelli-type reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds was studied in detail. We found that the reaction requires no catalysts and proceeds in boiling DMF to give 2-aryl-6-RC(O)-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carbonitriles in good yields. The reaction of aminopyrazoles with dicarbonyls leading to 6-unsubstituted pyrazolo[1,5-a]pyrimidines proceeds competitively and becomes the dominant process under acid-promoted conditions. 2-Aryl-8-oxo-4,5,6,7,8,9-hexahydropyrazolo[5,1-b]quinazolin-3-carbonitriles were obtained under catalyst-free conditions in up to 80% yields starting from 5-amino-3-arylpyrazole-4-carbonitriles, aldehydes and 1,3-cyclohexanedione 2018-11-16T09:43:46Z 2018-11-16T09:43:46Z 2016 Статья Kolosov, M.A., Beloborodov, D.A., Orlov, V.D., Dotsenko, V.V. Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines // New Journal of Chemistry. - 2016. - Volume 40. - Issue 9. - Pages 7573-7579 https://www.scopus.com/record/display.uri?eid=2-s2.0-84985023389&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=4deb6b7c4ec3f54375d585c101df8694&sot=afnl&sdt=sisr&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Catalyst-free+Biginelli-type+synthesis+of+new+functionalized+4%2c7-dihydropyrazolo%5b1%2c5-%3a+A%5d+pyrimidines%29&relpos=0&citeCnt=2&searchTerm= http://hdl.handle.net/20.500.12258/3429 en New Journal of Chemistry application/pdf application/pdf Royal Society of Chemistry |
| institution |
СКФУ |
| collection |
Репозиторий |
| language |
English |
| topic |
Aldehyde derivative Carbene Carbonyl derivative Cyanide Cyclohexane derivative Pyrazolopyrimidine derivative Quinazoline derivative Synthesis |
| spellingShingle |
Aldehyde derivative Carbene Carbonyl derivative Cyanide Cyclohexane derivative Pyrazolopyrimidine derivative Quinazoline derivative Synthesis Dotsenko, V. V. Доценко, В. В. Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| description |
The Biginelli-type reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds was studied in detail. We found that the reaction requires no catalysts and proceeds in boiling DMF to give 2-aryl-6-RC(O)-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carbonitriles in good yields. The reaction of aminopyrazoles with dicarbonyls leading to 6-unsubstituted pyrazolo[1,5-a]pyrimidines proceeds competitively and becomes the dominant process under acid-promoted conditions. 2-Aryl-8-oxo-4,5,6,7,8,9-hexahydropyrazolo[5,1-b]quinazolin-3-carbonitriles were obtained under catalyst-free conditions in up to 80% yields starting from 5-amino-3-arylpyrazole-4-carbonitriles, aldehydes and 1,3-cyclohexanedione |
| format |
Статья |
| author |
Dotsenko, V. V. Доценко, В. В. |
| author_facet |
Dotsenko, V. V. Доценко, В. В. |
| author_sort |
Dotsenko, V. V. |
| title |
Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| title_short |
Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| title_full |
Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| title_fullStr |
Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| title_full_unstemmed |
Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines |
| title_sort |
catalyst-free biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: a] pyrimidines |
| publisher |
Royal Society of Chemistry |
| publishDate |
2018 |
| url |
https://www.scopus.com/record/display.uri?eid=2-s2.0-84985023389&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=4deb6b7c4ec3f54375d585c101df8694&sot=afnl&sdt=sisr&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Catalyst-free+Biginelli-type+synthesis+of+new+functionalized+4%2c7-dihydropyrazolo%5b1%2c5-%3a+A%5d+pyrimidines%29&relpos=0&citeCnt=2&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/3429 |
| work_keys_str_mv |
AT dotsenkovv catalystfreebiginellitypesynthesisofnewfunctionalized47dihydropyrazolo15apyrimidines AT docenkovv catalystfreebiginellitypesynthesisofnewfunctionalized47dihydropyrazolo15apyrimidines |
| _version_ |
1760602122979639296 |