An efficient strategy for the synthesis of asymmetrically substituted enediynes fused to benzothiophene, benzofuran, and indole was developed. The proposed approach is based on the electrophilic cyclization of diacetylenes and Sonogashira coupling. Thus, iodocyclization of readily available ortho-functionalized (buta-1,3-diynyl)arenes was used as a direct way for the synthesis of 2-ethynyl-3-iodoheteroindenes. These substrates and their modified derivatives were easily converted by Sonogashira coupling with acetylenes to a variety of asymmetrically substituted acyclic enediynes fused to heterocycles. The tolerance of the developed methodology to a variety of functional groups is a great advantage in the synthesis of macrocyclic enediyne systems fused to a heterocyclic core. Synthesis of indole-fused 12-membered macrocyclic dienediyne was achieved using ring-closing metathesis as a key step.
a b s t r a c tAn efficient modular approach toward medicinally important 5-acylamino-4,5-isoxazolines via the 1,3-dipolar cycloaddition reaction of nitrile oxides and MCR-derived enamide building blocks is described. This approach results in isoxazolines containing four elements of diversity utilizing two practically simple synthetic operations.
Аннотация. В обзоре рассматриваются примеры внутримолекулярных цикли-заций с участием функционализированных диацетиленов. Циклизации протекают с участием одной из тройных связей с образованием этинилзамещенных гетеро-циклов или двух тройных связей, что используется в синтезе поликонденсирован-ных гетероциклических систем и ансамблей.Ключевые слова: бута-1,3-диины, внутримолекулярные циклизации, бисцик-лизации, этинилзамещенные гетероциклы, индолы, бензофураны, бензотиофены, индозолы, аннелированные поли гетероциклы.
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