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Synthesis of Azocane- and Oxocane-Annulated Furans by a [2+2] Photocycloaddition–Ring-Opening Cascade
Synthesis ( IF 2.2 ) Pub Date : 2020-11-05 , DOI: 10.1055/s-0040-1705957
Thorsten Bach 1 , Xinyao Li , Christian Jandl
Affiliation  

The title compounds were synthesized from readily available quinolone and coumarin derivatives by a cascade reaction (12 examples, 90–98% yield). The cascade comprised a [2+2] photocycloaddition which occurred upon sensitized irradiation at λ = 420 nm (or direct UV irradiation at λ = 366 nm) and a subsequent acid-catalyzed ring-opening reaction. A variety of substituents are compatible with the conditions and a 3-alkyl group in the coumarin (or quinolone) is crucial to achieve a high chemoselectivity. Key to the success of the ring opening is the formation of a 4,5,5a-trihydrocyclobuta-2H-furan containing a strained bridgehead double bond which stems from the allenyl group tethered to the 4-position of the starting materials.



中文翻译:

[2 + 2]光环加成-环-开口级联反应合成氮烷和氧烷环呋喃

通过级联反应,由容易获得的喹诺酮和香豆素衍生物合成标题化合物(12个实例,收率90-98%)。级联包含[2 + 2]光环加成,该加成发生在λ= 420 nm的敏化辐射(或λ= 366 nm的直接紫外线辐射)和随后的酸催化开环反应中。多种取代基与条件相容,香豆素(或喹诺酮)中的3-烷基对于实现高化学选择性至关重要。开环成功的关键是形成一个4,5,5a-三氢环丁2 H-呋喃,它含有一个应变的桥头双键,该双键源于拴在起始材料4位上的烯基。

更新日期:2020-11-06
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