Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes | Zendy

Lygin Alexander V. | Zendy; Larionov Oleg V. | Zendy; Korotkov Vadim S. | Zendy; de Meijere Armin | Zendy

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Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes

Author(s) -

Lygin Alexander V.,

Larionov Oleg V.,

Korotkov Vadim S.,

de Meijere Armin

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200801395

Subject(s) - cycloaddition , chemistry , yield (engineering) , triple bond , rationalization (economics) , combinatorial chemistry , medicinal chemistry , organic chemistry , double bond , catalysis , materials science , philosophy , epistemology , metallurgy

The formal cycloaddition of α‐metallated methyl isocyanides 1 onto the triple bond of electron‐deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3 . The scope and limitations of this reaction (24 examples, 25–97 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed Cu I ‐mediated synthesis of 2,3‐disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5–88 %yield).

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