Brønsted-acid-catalyzed one-pot tandem annulation/[5 + 2]-cycloaddition of o-propargyl alcohol benzaldehydes with alkynes: regioselective and stereoselective synthesis of dibenzo[a,f]azulen-12-ones,Organic Chemistry Frontiers

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Brønsted-acid-catalyzed one-pot tandem annulation/[5 + 2]-cycloaddition of o-propargyl alcohol benzaldehydes with alkynes: regioselective and stereoselective synthesis of dibenzo[a,f]azulen-12-ones
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2020-08-06 , DOI: 10.1039/d0qo00522c
Ni-Ni Zhou _{1,

2,

3,

4,

5} , Si-Si Ning _{1,

2,

3,

4,

5} , Lin-Qiang Li _{1,

2,

3,

4,

5} , Jie-Yun Zhang _{1,

2,

3,

4,

5} , Ming-Jin Fan _{1,

2,

3,

4,

5} , De-Suo Yang _{1,

2,

3,

4,

5} , Hai-Tao Zhu _{1,

2,

3,

4,

5}

Affiliation

The one-pot synthesis of dibenzo[a,f]azulen-12-ones has been established starting from o-propargyl alcohol benzaldehydes and alkynes. The key azulenone bicyclic skeletons were formed through the intramolecular tandem cyclization and intermolecular [5 + 2]-cycloaddition sequence. This annulation process showed high atom and step economy, regioselectivity and stereoselectivity by creating three C–C and one C–O bonds.

中文翻译：

布朗斯台德酸催化一锅串联环化/邻炔丙醇苯甲醛与炔烃的[5 + 2]-环加成反应：区域选择性和立体选择性合成二苯并[a，f] azulen-12-ones

从邻-炔丙基醇苯甲醛和炔烃开始，已经建立了一锅合成二苯并[ a，f ] azulen-12-ones 。关键的天青酮双环骨架是通过分子内串联环化和分子间[5 + 2]-环加成序列形成的。通过形成三个C–C和一个C–O键，这种成环过程显示出较高的原子和步长经济性，区域选择性和立体选择性。

更新日期：2020-09-16

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