{"title":"通过无催化剂多米诺反应前所未有地合成吲哚连接的四取代烯烃","authors":"Darakshan, Ujjain Chaurasia, Aatka Mehar, Tasneem Parvin","doi":"10.1016/j.tet.2024.134327","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we report a simple, efficient catalyst-free green domino reaction of indole, arylglyoxal, and cyclic 1,3-dicarbonyls such as barbituric acid derivatives/dimedone at 100 °C in dimethylformamide medium in open air condition. In this reaction, one C–C and one C<img>C bonds have been formed in one-pot without using any additive or metal based reagent. Considering the presence of indole, benzoyl and cyclic 1,3-dicarbonyl moieties in the products, it is expected that they will exhibit interesting medicinal properties. All the synthesized products were characterized by recording FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. Moreover, a single crystal XRD of compound <strong>4</strong><strong>j</strong> was recorded to confirm the structure of the product. Operational simplicity, gram-scale synthesis, mild reaction conditions, good yields, and wide substrate scope are the salient features of this methodology.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134327"},"PeriodicalIF":2.1000,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Unprecedented synthesis of indole-linked tetra-substituted alkenes by catalyst-free domino reaction\",\"authors\":\"Darakshan, Ujjain Chaurasia, Aatka Mehar, Tasneem Parvin\",\"doi\":\"10.1016/j.tet.2024.134327\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we report a simple, efficient catalyst-free green domino reaction of indole, arylglyoxal, and cyclic 1,3-dicarbonyls such as barbituric acid derivatives/dimedone at 100 °C in dimethylformamide medium in open air condition. In this reaction, one C–C and one C<img>C bonds have been formed in one-pot without using any additive or metal based reagent. Considering the presence of indole, benzoyl and cyclic 1,3-dicarbonyl moieties in the products, it is expected that they will exhibit interesting medicinal properties. All the synthesized products were characterized by recording FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. Moreover, a single crystal XRD of compound <strong>4</strong><strong>j</strong> was recorded to confirm the structure of the product. Operational simplicity, gram-scale synthesis, mild reaction conditions, good yields, and wide substrate scope are the salient features of this methodology.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"168 \",\"pages\":\"Article 134327\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-10-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024005088\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005088","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Unprecedented synthesis of indole-linked tetra-substituted alkenes by catalyst-free domino reaction
Herein, we report a simple, efficient catalyst-free green domino reaction of indole, arylglyoxal, and cyclic 1,3-dicarbonyls such as barbituric acid derivatives/dimedone at 100 °C in dimethylformamide medium in open air condition. In this reaction, one C–C and one CC bonds have been formed in one-pot without using any additive or metal based reagent. Considering the presence of indole, benzoyl and cyclic 1,3-dicarbonyl moieties in the products, it is expected that they will exhibit interesting medicinal properties. All the synthesized products were characterized by recording FTIR, 1H NMR, 13C NMR, and HRMS. Moreover, a single crystal XRD of compound 4j was recorded to confirm the structure of the product. Operational simplicity, gram-scale synthesis, mild reaction conditions, good yields, and wide substrate scope are the salient features of this methodology.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.