Raji Reddy Chada, Dilipkumar Uredi, Shravya Ravula
Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
Chem Commun (Camb). 2017 Feb 2;53(11):1904-1907. doi: 10.1039/c6cc09108c.
A novel one-pot benzannulation reaction has been developed for the synthesis of substituted polycyclic aromatic hydrocarbons (PAHs) from the direct coupling of propargylic aldehydes/alcohols with 1,1-diarylethanol through an atom-economical uninterrupted three/four-step reaction sequence under mild and metal-free reaction conditions. The strategy involves an acid-catalyzed dehydration and carbon-carbon bond formation followed by DBU-promoted cycloisomerization. Naphthalene and phenanthrene were obtained via mono-benzannulation, and chrysene, picene and benzopicene were obtained involving consecutive di-benzannulation reactions in good yields starting from easily accessible starting materials.
已经开发出一种新型的一锅法苯并环化反应，用于在温和且无金属的反应条件下，通过炔丙基醛/醇与1,1-二芳基乙醇的直接偶联，经原子经济的不间断三/四步反应序列合成取代的多环芳烃（PAHs）。该策略包括酸催化的脱水和碳-碳键形成，随后是DBU促进的环异构化。从易于获得的起始原料出发，通过单苯并环化反应得到萘和菲，通过连续的双苯并环化反应以良好的产率得到芘、苝和苯苝。
