M. D. Gotsko, I. V. Saliy, D. N. Tomilin, Yu. A. Ogloblina, I. A. Ushakov
{"title":"酰基乙基吡咯和吡咯丙酸酯与肼的相互作用:吡咯乙基酰肼和吡咯-吡唑系综的合成","authors":"M. D. Gotsko, I. V. Saliy, D. N. Tomilin, Yu. A. Ogloblina, I. A. Ushakov","doi":"10.1134/S1070428025602675","DOIUrl":null,"url":null,"abstract":"<p>2-Acylethynylpyrroles cyclize with hydrazines (hydrazine hydrate and phenylhydrazine, EtOH, 40°C, 0.5 h) to form pyrrolylpyrazoles in 63–95% yield. Unlike acylethynylpyrroles, pyrrolylpropynoates react with hydrazine hydrate and phenylhydrazine differently: interaction with hydrazine hydrate at a low temperature (EtOH, 0°C, 1 h) leads to the selective formation of pyrrolylethynylhydrazides (yield, 90–97%), whereas under reflux (EtOH, 1 h) in reactions with hydrazine and phenylhydrazine pyrrolylpyrazolones or pyrrolylpyrazolones are formed (yield, 88–97%).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1157 - 1171"},"PeriodicalIF":0.9000,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Interaction of Acylethynyl Pyrroles and Pyrrolyl Propynoates with Hydrazines: Synthesis of Pyrrolylethynyl Hydrazides and Pyrrol–Pyrazole Ensembles\",\"authors\":\"M. D. Gotsko, I. V. Saliy, D. N. Tomilin, Yu. A. Ogloblina, I. A. Ushakov\",\"doi\":\"10.1134/S1070428025602675\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>2-Acylethynylpyrroles cyclize with hydrazines (hydrazine hydrate and phenylhydrazine, EtOH, 40°C, 0.5 h) to form pyrrolylpyrazoles in 63–95% yield. Unlike acylethynylpyrroles, pyrrolylpropynoates react with hydrazine hydrate and phenylhydrazine differently: interaction with hydrazine hydrate at a low temperature (EtOH, 0°C, 1 h) leads to the selective formation of pyrrolylethynylhydrazides (yield, 90–97%), whereas under reflux (EtOH, 1 h) in reactions with hydrazine and phenylhydrazine pyrrolylpyrazolones or pyrrolylpyrazolones are formed (yield, 88–97%).</p>\",\"PeriodicalId\":766,\"journal\":{\"name\":\"Russian Journal of Organic Chemistry\",\"volume\":\"61 6\",\"pages\":\"1157 - 1171\"},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2025-07-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1070428025602675\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428025602675","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Interaction of Acylethynyl Pyrroles and Pyrrolyl Propynoates with Hydrazines: Synthesis of Pyrrolylethynyl Hydrazides and Pyrrol–Pyrazole Ensembles
2-Acylethynylpyrroles cyclize with hydrazines (hydrazine hydrate and phenylhydrazine, EtOH, 40°C, 0.5 h) to form pyrrolylpyrazoles in 63–95% yield. Unlike acylethynylpyrroles, pyrrolylpropynoates react with hydrazine hydrate and phenylhydrazine differently: interaction with hydrazine hydrate at a low temperature (EtOH, 0°C, 1 h) leads to the selective formation of pyrrolylethynylhydrazides (yield, 90–97%), whereas under reflux (EtOH, 1 h) in reactions with hydrazine and phenylhydrazine pyrrolylpyrazolones or pyrrolylpyrazolones are formed (yield, 88–97%).
期刊介绍:
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.