在常温下无能障合成六氮杂-三呋喃环十五烷-己烯

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-09-18 DOI:10.1021/acs.orglett.4c03064

Arvind Singh Chauhan, Ajay Kumar, Rohit Bains, Mahender Kumar, Navneet Sharma, Kousik Giri, Pralay Das

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摘要

我们在常温下合成了一种热化学稳定的呋喃基六氮杂-三呋喃环十五烷-六烯（AF-cpdp），它是π1212环共轭富色杂环。该研究采用经典的机械化学方法，避免外部加热，对 2,5-二甲酰基呋喃（DFF）与水合肼（N2H4-H2O）进行无能障（EBL）脱水偶氮形成，然后在最后一步进行单臂异共轭和成环，从而构建了一种新型且高度稳定的环十五烷（cpdp）共轭体系。所开发的方案简单、节能、原子经济、易于推广。

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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.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

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.