{"title":"在常温下无能障合成六氮杂-三呋喃环十五烷-己烯","authors":"Arvind Singh Chauhan, Ajay Kumar, Rohit Bains, Mahender Kumar, Navneet Sharma, Kousik Giri, Pralay Das","doi":"10.1021/acs.orglett.4c03064","DOIUrl":null,"url":null,"abstract":"A thermochemically stable furan-based hexaaza-trifuranacyclopentadecaphane-hexaene (AF-cpdp) as a π<sub>12</sub><sup>12</sup> cyclic-conjugated color enriched heterocycle has been synthesized at ambient temperature. An energy-barrier-less (EBL) dehydrative azine formation of 2,5-diformylfuran (DFF) with hydrazine hydrate (N<sub>2</sub>H<sub>4</sub>·H<sub>2</sub>O) followed by a single-arm heteroconjugation and ring formation at the final step under classical and mechanochemical approaches, avoiding external heating, was conducted for construction of a novel and highly stable cyclopentadecaphene (cpdp) conjugated system. The developed protocol is simple, energy-efficient, atom-economical, and easy to scale-up.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Energy-Barrier-less Synthesis of Hexaaza-trifuranacyclopentadecaphane-hexaene at Ambient Temperature\",\"authors\":\"Arvind Singh Chauhan, Ajay Kumar, Rohit Bains, Mahender Kumar, Navneet Sharma, Kousik Giri, Pralay Das\",\"doi\":\"10.1021/acs.orglett.4c03064\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A thermochemically stable furan-based hexaaza-trifuranacyclopentadecaphane-hexaene (AF-cpdp) as a π<sub>12</sub><sup>12</sup> cyclic-conjugated color enriched heterocycle has been synthesized at ambient temperature. An energy-barrier-less (EBL) dehydrative azine formation of 2,5-diformylfuran (DFF) with hydrazine hydrate (N<sub>2</sub>H<sub>4</sub>·H<sub>2</sub>O) followed by a single-arm heteroconjugation and ring formation at the final step under classical and mechanochemical approaches, avoiding external heating, was conducted for construction of a novel and highly stable cyclopentadecaphene (cpdp) conjugated system. The developed protocol is simple, energy-efficient, atom-economical, and easy to scale-up.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-09-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c03064\",\"RegionNum\":1,\"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":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03064","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Energy-Barrier-less Synthesis of Hexaaza-trifuranacyclopentadecaphane-hexaene at Ambient Temperature
A thermochemically stable furan-based hexaaza-trifuranacyclopentadecaphane-hexaene (AF-cpdp) as a π1212 cyclic-conjugated color enriched heterocycle has been synthesized at ambient temperature. An energy-barrier-less (EBL) dehydrative azine formation of 2,5-diformylfuran (DFF) with hydrazine hydrate (N2H4·H2O) followed by a single-arm heteroconjugation and ring formation at the final step under classical and mechanochemical approaches, avoiding external heating, was conducted for construction of a novel and highly stable cyclopentadecaphene (cpdp) conjugated system. The developed protocol is simple, energy-efficient, atom-economical, and easy to scale-up.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.