Iodine-mediated electrophilic cyclization of 2-alkynyl-1-methylene azide aromatics leading to highly substituted isoquinolines and its application to the synthesis of …
D Fischer, H Tomeba, NK Pahadi, NT Patil…
Index: Fischer, Dirk; Tomeba, Hisamitsu; Pahadi, Nirmal K.; Patil, Nitin T.; Huo, Zhibao; Yamamoto, Yoshinori Journal of the American Chemical Society, 2008 , vol. 130, # 46 p. 15720 - 15725
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Citation Number: 139
Abstract
The reaction of 2-alkynyl-1-methylene azide aromatics 1 with iodine and/or other iodium donors, such as the Barluenga reagent (Py2IBF4/HBF4) and NIS, gave highly substituted cyclization products, namely, the 1, 3-disubstituted 4-iodoisoquinolines 2, in good to high yields. Not only simple 2-alkynyl benzyl azides 1a− j and their substituted analogues 1k− u and 6 but also heteroaromatic analogues, including pyridine 8, pyrroles 10a− c, furane ...
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