{"title":"Utilization of <i>N</i>-acyl compounds for the synthesis of tricyclic and bridged heterocyclic compounds.","authors":"Mohamed A Waly, Fawzia Z El-Ablack","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>N-acyl derivative <b>4</b> was prepared via the reaction of methyl anthranilate with ethyl bromoacetate then refluxing the formed amino ester <b>3</b> with acetic anhydride. Cyclization of <b>4</b> in presences of sodium methoxide and methanol forming 2,4-pyrrolidindione derivative <b>5</b>. 2,4-Quinolidinone <b>6</b> was obtained via cyclization of <b>4</b> in dry toluene and sodium hydride. On the other hand, indolinone derivative <b>8</b> was obtained by cyclization of <b>4</b> in toluene and free from alcohol due to retro Diekmann-condensation. On treatment of <b>8</b> with sodium hydride, refluxing toluene and in presences of Crown ether gave tricyclic compound <b>9</b>. Also, treatment of 2-pyrrolidinone with trimethylene chlorobromide produced <b>10</b> which cyclized using base and solvent to the bridged ring derivatives <b>11</b>. The acidic hydrolysis of <b>11</b> afforded the corresponding amino acid <b>13</b>. Whereas derivative <b>14</b> was obtained by the reaction of 2-pyrrolidinone with ethyl 3-bromopropionate which on cyclization gave azabicyclo[3,2,1]octan-4,8-dione derivative <b>15</b>. Compound <b>15</b> underwent acidic hydrolysis to the amino ketone derivative azepanone hydrochloride <b>17</b>.</p>","PeriodicalId":12555,"journal":{"name":"Global journal of chemistry","volume":"1 1","pages":"21-27"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34279242","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}