B. Banerjee, M. Kaur, Aditi Sharma, Ashutosh Kumar Singh, A. Priya, V. Gupta, V. Jaitak
{"title":"甘氨酸催化回流条件下乙醇水溶液一锅三组分合成结构多样的2-氨基取代吡喃环杂环","authors":"B. Banerjee, M. Kaur, Aditi Sharma, Ashutosh Kumar Singh, A. Priya, V. Gupta, V. Jaitak","doi":"10.2174/2213346110666221212152202","DOIUrl":null,"url":null,"abstract":"\n\nA facile, convenient and general method has been developed for the one-pot three-component synthesis of structurally diverse 2-amino pyran annulated heterocycles from the reactions of aromatic aldehydes, malononitrile and various C-H activated acids in the presence of a catalytic amount of glycine as an efficient metal-free organocatalyst in aqueous ethanol under refluxed conditions.\n\n\n\nUsing this developed protocol, we were able to synthesize a series of structurally diverse 2-amino pyran derivatives viz., 2-amino-4,5-dihydropyrano[3,2-c]chromenes, 2-amino-4,5-dihydropyrano[4,3-b]pyrans, 2-amino-5,6,7,8-tetrahydro-4H-chromenes, 2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile and 2'-amino-1,3,5'-trioxo-1,3-dihydro-5'H-spiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile in excellent yields.\n\n\n\nSynthesis of biologically promising pyrans and spiropyrans, high atom economy, excellent yields, use of metal-free catalyst, less toxic solvents, no chromatographic column purifications, multiple carbon-carbon and carbon-heteroatom bond formations are some of the major advantages of this newly developed protocol.\n","PeriodicalId":10856,"journal":{"name":"Current Green Chemistry","volume":null,"pages":null},"PeriodicalIF":1.1000,"publicationDate":"2022-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":"{\"title\":\"Glycine catalyzed one-pot three-component synthesis of structurally diverse 2-amino substituted pyran annulated heterocycles in aqueous ethanol under refluxed conditions\",\"authors\":\"B. Banerjee, M. Kaur, Aditi Sharma, Ashutosh Kumar Singh, A. Priya, V. Gupta, V. Jaitak\",\"doi\":\"10.2174/2213346110666221212152202\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"\\n\\nA facile, convenient and general method has been developed for the one-pot three-component synthesis of structurally diverse 2-amino pyran annulated heterocycles from the reactions of aromatic aldehydes, malononitrile and various C-H activated acids in the presence of a catalytic amount of glycine as an efficient metal-free organocatalyst in aqueous ethanol under refluxed conditions.\\n\\n\\n\\nUsing this developed protocol, we were able to synthesize a series of structurally diverse 2-amino pyran derivatives viz., 2-amino-4,5-dihydropyrano[3,2-c]chromenes, 2-amino-4,5-dihydropyrano[4,3-b]pyrans, 2-amino-5,6,7,8-tetrahydro-4H-chromenes, 2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile and 2'-amino-1,3,5'-trioxo-1,3-dihydro-5'H-spiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile in excellent yields.\\n\\n\\n\\nSynthesis of biologically promising pyrans and spiropyrans, high atom economy, excellent yields, use of metal-free catalyst, less toxic solvents, no chromatographic column purifications, multiple carbon-carbon and carbon-heteroatom bond formations are some of the major advantages of this newly developed protocol.\\n\",\"PeriodicalId\":10856,\"journal\":{\"name\":\"Current Green Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.1000,\"publicationDate\":\"2022-12-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"5\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current Green Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.2174/2213346110666221212152202\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Green Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/2213346110666221212152202","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Glycine catalyzed one-pot three-component synthesis of structurally diverse 2-amino substituted pyran annulated heterocycles in aqueous ethanol under refluxed conditions
A facile, convenient and general method has been developed for the one-pot three-component synthesis of structurally diverse 2-amino pyran annulated heterocycles from the reactions of aromatic aldehydes, malononitrile and various C-H activated acids in the presence of a catalytic amount of glycine as an efficient metal-free organocatalyst in aqueous ethanol under refluxed conditions.
Using this developed protocol, we were able to synthesize a series of structurally diverse 2-amino pyran derivatives viz., 2-amino-4,5-dihydropyrano[3,2-c]chromenes, 2-amino-4,5-dihydropyrano[4,3-b]pyrans, 2-amino-5,6,7,8-tetrahydro-4H-chromenes, 2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile and 2'-amino-1,3,5'-trioxo-1,3-dihydro-5'H-spiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile in excellent yields.
Synthesis of biologically promising pyrans and spiropyrans, high atom economy, excellent yields, use of metal-free catalyst, less toxic solvents, no chromatographic column purifications, multiple carbon-carbon and carbon-heteroatom bond formations are some of the major advantages of this newly developed protocol.