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首页> 外文期刊>Chemistry: A European journal >Synthesis of meso-Pyrrole-Substituted 22-Oxacorroles by a “3+2” Approach
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Synthesis of meso-Pyrrole-Substituted 22-Oxacorroles by a “3+2” Approach

机译：通过“ 3 + 2”方法合成内消旋吡咯取代的22-氧戊酸酯

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摘要

Unsymmetrical 22-oxacorrole containing two aryl groups and one pyrrole group at the meso position was synthesized by condensing one equivalent of 16-oxatripyrrane with one equivalent of meso aryl dipyromethane under mild acid-catalyzed conditions followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). This [3+2] condensation approach was expected to yield meso-free 25-oxasmaragdyrin but unexpectedly afforded unsymmetrical meso-pyrrole-substituted 22-oxacorrole. We demonstrated the versatility of the reaction by synthesizing four new meso-pyrrole-substituted 22-oxacorroles. The reactivity of aposition of meso-pyrrole was tested by carrying out various functionalization reactions such as bromination, formylation, and nitration and obtained the functionalized meso-pyrrolesubstituted 22-oxacorroles in decent yields. The X-ray structure obtained for one of the functionalized meso-pyrrole substituted 22-oxacorrole revealed that the macrocycle was nearly planar and the meso-pyrrole was in the perpendicular orientation with respect to the macrocyclic plane. The mesopyrrole-substituted 22-oxacorroles absorb strongly in 400–700 nm region with one strong Soret band and four weak Q bands. The 22-oxacorroles are strongly fluorescent and showed emission maxima at ≈650 nm with decent quantum yields and singlet-state lifetimes. The 22-oxacorroles are redox-active and exhibited three irreversible oxidations and one or two reversible reduction(s). A preliminary biological study indicated that meso-pyrrole corroles are biocompatible.
机译：通过在温和的酸催化条件下，将1当量的16-氧杂三吡喃与1当量的内消旋芳基二吡咯甲烷缩合，然后用2,3-二氯-5进行氧化，合成不对称的22-恶唑环，在中位含有两个芳基和一个吡咯基。 ，6-二氰基-1,4-苯醌（DDQ）。预计这种[3 + 2]缩合方法可生成无内消旋的25-氧杂mar啶，但出乎意料地提供了不对称的由内吡咯取代的22-恶二唑。我们通过合成四个新的内消旋吡咯取代的22-氧杂咯啉证明了反应的多功能性。通过进行各种官能化反应，例如溴化，甲酰化和硝化反应，测试了介孔吡咯的位置的反应性，并以适当的产率获得了官能化的介孔吡咯取代的22-恶唑。对于官能化的中吡咯取代的22-恶二唑之一，获得的X射线结构表明大环几乎是平面的，并且中吡咯相对于大环平面垂直。甲基吡咯取代的22-氧杂咯啉在400-700 nm区域吸收强，有一个强Soret带和四个弱Q带。 22-氧杂戊酸酯具有很强的荧光性，并在≈650nm处显示出最大值，并具有可观的量子产率和单线态寿命。 22-氧杂甲酚具有氧化还原活性，并表现出三个不可逆的氧化和一个或两个可逆的还原。初步的生物学研究表明，中吡咯酯具有生物相容性。

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