Green synthesis of novel hexahydroquinolines and 6-amino-2-oxopyridine-3,5-dicarbonitriles incorporating sulfaguanidine via [3 + 3] atom combination

IF 2.5 Q2 CHEMISTRY, MULTIDISCIPLINARY

Results in Chemistry Pub Date : 2025-01-22 DOI:10.1016/j.rechem.2025.102065

Amr M. Abdelmoniem , Mostafa E. Salem , Mahmoud Hassan Mohamed Allam , Mortaga M. Abou-Krisha , Ibrahim O. Althobaiti , Said A.S. Ghozlan , Khaled E. Azmy , Ismail A. Abdelhamid

{"title":"Green synthesis of novel hexahydroquinolines and 6-amino-2-oxopyridine-3,5-dicarbonitriles incorporating sulfaguanidine via [3 + 3] atom combination","authors":"Amr M. Abdelmoniem , Mostafa E. Salem , Mahmoud Hassan Mohamed Allam , Mortaga M. Abou-Krisha , Ibrahim O. Althobaiti , Said A.S. Ghozlan , Khaled E. Azmy , Ismail A. Abdelhamid","doi":"10.1016/j.rechem.2025.102065","DOIUrl":null,"url":null,"abstract":"<div><div>The synthesis of sulfa drugs has received extensive interest from researchers for their broad spectrum of biological activities. In this context, <em>N</em>-Carbamimidoyl-4-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)benzenesulfonamide <strong>3</strong> was readily prepared and its Michael addition reactions towards activated cinnamonitriles were studied as a route to 4-(2-amino-3-cyano-4-aryl-tetrahydroquinolin-1-yl)-<em>N</em>-carbamimidoylbenzenesulfonamide derivatives <strong>8a-d</strong>. Moreover, <em>N</em>-(4-(<em>N</em>-carbamimidoylsulfamoyl)phenyl)-2-cyanoacetamide <strong>13</strong> was prepared and employed as a precursor for the synthesis of 4-(6-amino-3,5-dicyano-2-oxo-4-arylpyridin-1-yl)-<em>N</em>-carbamimidoylbenzenesulfonamide derivatives <strong>17a-e</strong>. Green synthesis of the targeted products was done in water in the presence of chitosan as a green catalyst and gave considerably higher yields as compared to conducting reactions in ethanol in presence of non-benign piperidine catalyst. The chemical constitution of all newly synthesized compounds was confirmed by the different spectral tools.</div></div>","PeriodicalId":420,"journal":{"name":"Results in Chemistry","volume":"14 ","pages":"Article 102065"},"PeriodicalIF":2.5000,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Results in Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2211715625000487","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

Abstract

The synthesis of sulfa drugs has received extensive interest from researchers for their broad spectrum of biological activities. In this context, N-Carbamimidoyl-4-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)benzenesulfonamide 3 was readily prepared and its Michael addition reactions towards activated cinnamonitriles were studied as a route to 4-(2-amino-3-cyano-4-aryl-tetrahydroquinolin-1-yl)-N-carbamimidoylbenzenesulfonamide derivatives 8a-d. Moreover, N-(4-(N-carbamimidoylsulfamoyl)phenyl)-2-cyanoacetamide 13 was prepared and employed as a precursor for the synthesis of 4-(6-amino-3,5-dicyano-2-oxo-4-arylpyridin-1-yl)-N-carbamimidoylbenzenesulfonamide derivatives 17a-e. Green synthesis of the targeted products was done in water in the presence of chitosan as a green catalyst and gave considerably higher yields as compared to conducting reactions in ethanol in presence of non-benign piperidine catalyst. The chemical constitution of all newly synthesized compounds was confirmed by the different spectral tools.

Abstract Image