Rh‐Catalyzed Transannulation of Pyridotriazoles with Alkynes and Nitriles.

Abstract

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Transition Metal Chemistry of Cyclopropenes and Cyclopropanes

“…Recently Gevorgyan developed a novel iminocyclopropene to pyrrole rearrangement, which represents an aza-analogue of acylcyclopropene to furan cycloisomerization reaction, described in section 2.3.2. 101 It was found that catalytic amounts of Rh(I) efficiently produced 1,3,5-trisubstituted indolizines 136, presumably via the rhodium vinylcarbenoid species 135 (Scheme 55). Remarkably, complementary regiochemistry of the cyclopropene ring cleavage was observed when the reaction was carried out in the presence of Cu(I) catalysts.…”

“…In this case, 2,3,5-trisubstituted indolizines 137 were obtained in excellent yields (Scheme 55). 101 Extension of this cycloisomerization methodology to other heterocyclic systems proved successful: under the same reaction conditions, oxazolylcyclopropene 138 was smoothly converted into pyrrolooxazole 139 (Scheme 56). 101…”