- Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment
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A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.
- Gao, Qinghe,Sun, Zhenhua,Xia, Qinfei,Li, Ruonan,Wang, Wenlong,Ma, Siwei,Chai, Yixin,Wu, Manman,Hu, Wei,ábrányi-Balogh, Péter,Keserü, Gy?rgy M.,Han, Xinya
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supporting information
p. 2664 - 2669
(2021/04/12)
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- Synthetic method of pyrazolopyrimidine compound
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The invention discloses a synthesis method of a pyrazolopyrimidine compound, and belongs to the technical field of organic synthesis. According to the technical scheme, the method is characterized by comprising the following steps: dissolving an aldehyde
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Paragraph 0010; 0077-0079
(2021/06/12)
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- Synthesis of a new series of pyrazolo[1,5-a]pyrimidines structurally related to zaleplon
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(Chemical Equation Presented) The reaction between 3-(dimethylamino)/3,3- bis(methylthio)-1-(substituted)prop-2-en-1-ones and 4-substituted-5-amino-1H- pyrazoles afforded new pyrazole[1,5-a]pyrimidines structurally related to Zaleplon. The chemical modifications introduced at the 3-, 5-, and 7-positions of the bicyclic structure revealed new promising candidates for the treatment of sleep disorders.
- Baraldi, Pier Giovanni,Fruttarolo, Francesca,Tabrizi, Mojgan Aghazadeh,Romagnoli, Romeo,Preti, Delia,Ongini, Ennio,El-Kashef, Hussein,Carrion, Maria Dora,Borea, Pier Andrea
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p. 355 - 361
(2008/04/12)
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- Substituted pyrazolo (1,5-a)pyrimidines and their use as anxiolytic agents
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This disclosure describes substituted pyrazolo[1,5-a]pyrimidines which possess anxiolytic activity.
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