S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan
{"title":"基于 2-氨基-4-(1,4-苯并二恶烷-2-基)噻吩-3-羧酸乙酯的取代型噻吩嘧啶酮的合成","authors":"S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan","doi":"10.1134/S1070428024030047","DOIUrl":null,"url":null,"abstract":"<p>Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-<i>d</i>]pyrimidin-4(1<i>H</i>)-ones by the action of hydrazine hydrate. The condensation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-aminothienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate\",\"authors\":\"S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan\",\"doi\":\"10.1134/S1070428024030047\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-<i>d</i>]pyrimidin-4(1<i>H</i>)-ones by the action of hydrazine hydrate. The condensation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-aminothienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.</p>\",\"PeriodicalId\":766,\"journal\":{\"name\":\"Russian Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2024-05-19\",\"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/S1070428024030047\",\"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/S1070428024030047","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate
Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-d]pyrimidin-4(1H)-ones by the action of hydrazine hydrate. The condensation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-aminothienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.
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.