New Efficient, Flexible and Regioselective Synthesis of 2,4‐Di‐ and 2,3,4‐Trialkylated an Arylated 1 H ‐Pyrroles | Zendy

Enders Dieter | Zendy; Maaßen Ralf | Zendy; Han SinHo | Zendy

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New Efficient, Flexible and Regioselective Synthesis of 2,4‐Di‐ and 2,3,4‐Trialkylated an Arylated 1 H ‐Pyrroles

Author(s) -

Enders Dieter,

Maaßen Ralf,

Han SinHo

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619961011

Subject(s) - umpolung , chemistry , regioselectivity , yield (engineering) , aldehyde , silylation , alkyl , enol , aryl , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , nucleophile , materials science , metallurgy

Starting from easily available 2‐acetoxy aldehyde dimethylhydrazones rac ‐ 2 , we prepared various alkyl‐ and aryl‐substituted 1 H ‐pyrroles 6 in good overall yield. The titariummediated a 2 ‐umpolung reaction of rac ‐ 2 with different acyclic and cyclic silyl enol ethers 3 leads directly or via 4‐oxo hydrazones rac,anti ‐ 4 to 1‐(dimethylamino)‐1 H ‐pyrroles 5 . A novel method for the reductive removal of the dimethylamino group affording 1 H ‐pyrroles 6 is presented.

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