1239487-53-6Relevant articles and documents
Facile synthesis of dihaloheterocycles via electrophilic iodocyclization
Yang, Fan,Jin, Tienan,Bao, Ming,Yamamoto, Yoshinori
, p. 10147 - 10155 (2012/01/03)
An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having -OH, -NTs, and -SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered heterocycles in good to high yields; Under optimized solvent conditions, the reactions of various substituted but-2-yn-1-ones bearing -OH, -NTs, and -SAc functional groups at C4-position, with iodine or bromoiodine at ambient temperature afforded the corresponding 3,4-diiodo- and 3-bromo-4-iodo-substituted furans, pyrroles, and thiophenes in good to high yields. Further transformation of the resulting iodine- or bromine-containing products to polyaromatics potentially of useful as organo-material intermediates has been investigated.
Synthesis of five- and six-membered dihalogenated heterocyclic compounds by electrophile-triggered cyclization
Ji, Ke-Gong,Zhu, Hai-Tao,Yang, Fang,Shaukat, Ali,Xia, Xiao-Feng,Yang, Yan-Fang,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; scheme or table, p. 5670 - 5678 (2010/11/05)
Highly substituted dihalogenated dihydrofurans, dihydropyrroles, and dihydro-2H-pyrans bearing alkyl, vinyl, aryl, and heteroaryl moieties can be prepared in good to excellent yields (up to 99%) by allowing 1,4-butyne-diol, 4-aminobut-2-yn-1-ol, and pent-2-yne-1,5-diol derivatives to react with different electrophiles (I2, IBr, and ICl) at room temperature. Both halogen atoms generated from electrophiles were used effectively. The resulting halides can be further exploited by using palladium-catalyzed coupling reactions. The presence of trace amount of water is essential for this electrophilic cyclization.