The present paper describes first an efficient methodology for an easy O-functionalization (alkylation) of tetracyclic hydroxyisoxazolines 1 applied to the synthesis of eight examples of new 3-(alkoxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno [4,3-c]isoxazole-4,1′-cycloalkanes] (6-9) at 61–84% yields, in which the alkoxy substituents were methoxy, benzyloxy, allyloxy, or prop-2-yn-1-yloxy; while the cycloalkanes were 5-, 6-, and 7-membered carbocycles, as well as 4′-methyl- and 4′-t-butyl-cyclohexane. The reaction medium used 1, four alkyl halides (2-5), K₂CO₃, and KI in DMF at room temperature. The selected 3-(prop-2-yn-1-yloxy)-substituted isoxazolines 6 were successfully used as a CC-fragment in the construction of another series of five examples of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1′-cycloalkanes] (10), at 36–84% yields, through a regioselective 1,3 dipolar cycloaddition reaction catalyzed by copper iodide (CuAAC), using benzyl azide as an NNN-building block (Click Chemistry).

本文首先介绍了一种有效的方法，用于四环羟基异恶唑啉1的简单O-官能化（烷基化），该方法可用于合成新的3-（烷氧基）-3-（三氟甲基）-3,3a-二氢螺基[chromeno [ 4,3 - c ]异恶唑-4,1'-环烷烃]（6-9）的产率为61–84％，其中烷氧基取代基为甲氧基，苄氧基，烯丙氧基或丙-2-炔-1-基氧基；而环烷烃是5、6和7元碳环以及4'-甲基和4'-叔丁基-环己烷。将反应介质用1，四烷基卤化物（2 - 5），K ₂ CO ₃，以及在室温下在DMF中使用KI。所选的3-（prop-2-yn-1-yloxy）-取代的异恶唑啉6成功地用作CC片段，用于构建3-（（1-苄基-1 H -1， 2,3-三唑-4-基）甲氧基）-3-（三氟甲基）-3,3a-二氢螺[铬色[4,3 - c ]异恶唑-4,1'-环烷烃]（10），在36–84通过使用叠氮化苄基作为NNN结构单元（点击化学），由碘化铜（CuAAC）催化的区域选择性1，3偶极环加成反应，得到3％的收率。