{"title":"用碳化钙作为炔源构建吡唑并[1,5-a]嘧啶和嘧啶并[1,2-b]吲唑。","authors":"Xinjie You, Botao Wang, Fei Wen, Zheng Li","doi":"10.1039/d4ob00881b","DOIUrl":null,"url":null,"abstract":"<p><p>An efficient method for the construction of 5-arylpyrazolo[1,5-<i>a</i>]pyrimidines using calcium carbide as a solid alkyne source instead of flammable and explosive gaseous acetylene, pyrazole-3-amine and (hetero)aromatic aldehydes as starting materials in the presence of a copper mediator is described. Meanwhile, 2-arylpyrimido[1,2-<i>b</i>]indazoles are also synthesized under similar conditions using indazole-3-amine as a substitute for pyrazole-3-amine as a starting material. The method has salient features such as the use of an inexpensive and easy-to-handle alkyne source, commercially available substrates, wide functional group tolerance, a low-cost mediator, and simple workup procedures. This protocol can also be extended to gram-scale synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Construction of pyrazolo[1,5-<i>a</i>]pyrimidines and pyrimido[1,2-<i>b</i>]indazoles with calcium carbide as an alkyne source.\",\"authors\":\"Xinjie You, Botao Wang, Fei Wen, Zheng Li\",\"doi\":\"10.1039/d4ob00881b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>An efficient method for the construction of 5-arylpyrazolo[1,5-<i>a</i>]pyrimidines using calcium carbide as a solid alkyne source instead of flammable and explosive gaseous acetylene, pyrazole-3-amine and (hetero)aromatic aldehydes as starting materials in the presence of a copper mediator is described. Meanwhile, 2-arylpyrimido[1,2-<i>b</i>]indazoles are also synthesized under similar conditions using indazole-3-amine as a substitute for pyrazole-3-amine as a starting material. The method has salient features such as the use of an inexpensive and easy-to-handle alkyne source, commercially available substrates, wide functional group tolerance, a low-cost mediator, and simple workup procedures. This protocol can also be extended to gram-scale synthesis.</p>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-07-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob00881b\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob00881b","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Construction of pyrazolo[1,5-a]pyrimidines and pyrimido[1,2-b]indazoles with calcium carbide as an alkyne source.
An efficient method for the construction of 5-arylpyrazolo[1,5-a]pyrimidines using calcium carbide as a solid alkyne source instead of flammable and explosive gaseous acetylene, pyrazole-3-amine and (hetero)aromatic aldehydes as starting materials in the presence of a copper mediator is described. Meanwhile, 2-arylpyrimido[1,2-b]indazoles are also synthesized under similar conditions using indazole-3-amine as a substitute for pyrazole-3-amine as a starting material. The method has salient features such as the use of an inexpensive and easy-to-handle alkyne source, commercially available substrates, wide functional group tolerance, a low-cost mediator, and simple workup procedures. This protocol can also be extended to gram-scale synthesis.