Vakhid A. Mamedov, Nataliya A. Zhukova, Victor V. Syakaev, Aidar T. Gubaidullin, Aida I. Samigullina, Tat’yana N. Beschastnova, Darya S. Perevalova, Olga B. Babaeva, Il′dar Kh. Rizvanov, Oleg G. Sinyashin
{"title":"AcOH 催化的苯并[e][1,4]二氮杂卓-2(和 3)-酮重排:轻松获得 1,4-二氢喹唑啉及其缩合类似物","authors":"Vakhid A. Mamedov, Nataliya A. Zhukova, Victor V. Syakaev, Aidar T. Gubaidullin, Aida I. Samigullina, Tat’yana N. Beschastnova, Darya S. Perevalova, Olga B. Babaeva, Il′dar Kh. Rizvanov, Oleg G. Sinyashin","doi":"10.1021/acs.joc.4c01721","DOIUrl":null,"url":null,"abstract":"Presented herein is a novel synthesis of new 2-(quinolin-4-yl)-1,4-dihydroquinazoline systems <b>8</b>, in which the acid-catalyzed rearrangement of spiro[benzo[<i>e</i>][1,4]diazepine-3,4′-quinolin]-2(1<i>H</i>)-ones generated <i>in situ</i> from 3-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-ones <b>6</b> with acetone and alkylmethyl ketones has been realized as an important step. An attempt to synthesize isomeric 2-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-one <b>6′a</b> by hydrolysis of the corresponding <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-on-2-yl]phenyl}acetamide <b>5′a</b> led to a new heterocyclic system, 6-methyl-8,13-dihydro-13a<i>H</i>-quinazolino[4,3-<i>b</i>]quinazolin-5-ium 13a-carboxylate <b>14</b>, as a result of an unexpected rearrangement. In addition, it is noteworthy that during the hydrolysis of <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-on-3-yl]phenyl}acetamides <b>5</b>, the not previously described 14-dihydro-5<i>H</i>-14,5a-(epimino[1,2]benzo)benzo[5,6][1,4]diazepin[2,1<i>-b</i>]quinazolin-6(7<i>H</i>)-ones <b>7</b> were unexpectedly obtained.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"AcOH-Catalyzed Rearrangements of Benzo[e][1,4]diazepin-2(and 3)-ones: Easy Access to 1,4-Dihydroquinazolines and Their Condensed Analogues\",\"authors\":\"Vakhid A. Mamedov, Nataliya A. Zhukova, Victor V. Syakaev, Aidar T. Gubaidullin, Aida I. Samigullina, Tat’yana N. Beschastnova, Darya S. Perevalova, Olga B. Babaeva, Il′dar Kh. Rizvanov, Oleg G. Sinyashin\",\"doi\":\"10.1021/acs.joc.4c01721\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Presented herein is a novel synthesis of new 2-(quinolin-4-yl)-1,4-dihydroquinazoline systems <b>8</b>, in which the acid-catalyzed rearrangement of spiro[benzo[<i>e</i>][1,4]diazepine-3,4′-quinolin]-2(1<i>H</i>)-ones generated <i>in situ</i> from 3-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-ones <b>6</b> with acetone and alkylmethyl ketones has been realized as an important step. An attempt to synthesize isomeric 2-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-one <b>6′a</b> by hydrolysis of the corresponding <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-on-2-yl]phenyl}acetamide <b>5′a</b> led to a new heterocyclic system, 6-methyl-8,13-dihydro-13a<i>H</i>-quinazolino[4,3-<i>b</i>]quinazolin-5-ium 13a-carboxylate <b>14</b>, as a result of an unexpected rearrangement. In addition, it is noteworthy that during the hydrolysis of <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-on-3-yl]phenyl}acetamides <b>5</b>, the not previously described 14-dihydro-5<i>H</i>-14,5a-(epimino[1,2]benzo)benzo[5,6][1,4]diazepin[2,1<i>-b</i>]quinazolin-6(7<i>H</i>)-ones <b>7</b> were unexpectedly obtained.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c01721\",\"RegionNum\":2,\"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":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01721","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
AcOH-Catalyzed Rearrangements of Benzo[e][1,4]diazepin-2(and 3)-ones: Easy Access to 1,4-Dihydroquinazolines and Their Condensed Analogues
Presented herein is a novel synthesis of new 2-(quinolin-4-yl)-1,4-dihydroquinazoline systems 8, in which the acid-catalyzed rearrangement of spiro[benzo[e][1,4]diazepine-3,4′-quinolin]-2(1H)-ones generated in situ from 3-(2-aminophenyl)-5H-benzo[e][1,4]diazepin-2(1H)-ones 6 with acetone and alkylmethyl ketones has been realized as an important step. An attempt to synthesize isomeric 2-(2-aminophenyl)-5H-benzo[e][1,4]diazepin-3(4H)-one 6′a by hydrolysis of the corresponding N-{2-[5H-benzo[e][1,4]diazepin-3(4H)-on-2-yl]phenyl}acetamide 5′a led to a new heterocyclic system, 6-methyl-8,13-dihydro-13aH-quinazolino[4,3-b]quinazolin-5-ium 13a-carboxylate 14, as a result of an unexpected rearrangement. In addition, it is noteworthy that during the hydrolysis of N-{2-[5H-benzo[e][1,4]diazepin-2(1H)-on-3-yl]phenyl}acetamides 5, the not previously described 14-dihydro-5H-14,5a-(epimino[1,2]benzo)benzo[5,6][1,4]diazepin[2,1-b]quinazolin-6(7H)-ones 7 were unexpectedly obtained.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.