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http://dx.doi.org/10.5012/bkcs.2009.30.6.1293

Synthesis of 2-n-Butyl-3-fluoropyrrole Derivatives  

Kim, Bo-Mi (Department of Bionanochemistry, Wonkwang University)
San, Quan-Ze (College of Pharmacy, Yanbian University)
Bhatt, Lok Ranjan (Department of Bionanochemistry, Wonkwang University)
Jung, Dong-Woon (Department of Bionanochemistry, Wonkwang University)
Lee, Young-Hang (Department of Bionanochemistry, Wonkwang University)
Chai, Kyu-Yun (Department of Bionanochemistry, Wonkwang University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.6, 2009 , pp. 1293-1296 More about this Journal
Abstract
A new series of N-substituted 2-n-butyl-3-fluoropyrroles were prepared by a simple one-pot reaction designed of retrosynthesis. $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl)propyl n-butyl ketone, a component precursor molecule to 2-n-butyl-3-fluoropyrroles, was prepared with Cu(0) catalyst. It reacted with various primary amines to yield N-substituted 2-n-butyl-3-fluoropyrroles. The products were synthesized via a one-pot reaction scheme between $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl) propyl n-butyl ketone and primary amines in excess ( $\geq$ 5 molar equivalence), which eliminate the need of KF required in obtaining n-butyl-1H-3-fluoropyrrole. The yield of products depended reversely on spatial bulkness around N-binding carbon.
Keywords
N-Substituted 2-n-butyl-3-fluoropyrroles; $\alpha$,$\alpha$-Difluoro-iodomethyl n-butylketone; 2,$\alpha$,$\alpha$-Difluoro-$\gamma$-iodo-$\gamma$-(trimethylsilyl)propyl n-butylketone; 2-Butyl-3,3-difluoro-5-trimethylsilyl pyrroline;
Citations & Related Records
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