Approach to extended polycyclic aromatic hydrocarbons by benzannulation and intramolecular cyclization; improvement of the reaction conditions by microwave irradiation

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-10-24 DOI:10.1016/j.tet.2024.134332
Rui Umeda, Raiki Nishikawa, Taketo Matsui, Kotaro Takase
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Abstract

The extended π-conjugated compounds 18 were synthesized by the benzannulation of the corresponding alkyne derivatives followed by Pd-catalyzed intramolecular cyclization. For the Pd-catalyzed intramolecular cyclization, microwave irradiation reduced the amount of the Pd catalyst and the reaction time. Moreover, this protocol can be achieved to prepare the extended and twisted π-conjugated molecule 19, having anthracene, helicene, and picene skeletons.

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通过苯annulation 和分子内环化反应制备扩展的多环芳烃;利用微波辐照改善反应条件
扩展的π-共轭化合物 1-8 是通过相应炔衍生物的苯并环化和钯催化的分子内环化合成的。在钯催化的分子内环化反应中,微波辐照减少了钯催化剂的用量和反应时间。此外,这种方法还可以制备出具有蒽、螺旋烯和皮烯骨架的扩展和扭曲的π-共轭分子 19。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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