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Synthesis of lipophilic lariat ethers with pendant N ‐(X)sulfonyl carboxamide groups
Author(s) -
Hu Hui,
Bartsch Richard A.
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410412
Subject(s) - chemistry , sulfonyl , carboxamide , trifluoromethyl , ring (chemistry) , ether , stereochemistry , crown (dentistry) , medicinal chemistry , organic chemistry , medicine , alkyl , dentistry
Synthetic routes to sixteen lipophilic lariat ether N ‐(X)sulfonyl carboxamides with X = trifluoromethyl, methyl, phenyl, and p ‐nitrophenyl are described. For this new family of proton‐ionizable lariat ethers in which the acidity can be ‘tuned’ by X group variation, the ring size is systematically varied from 12‐crown‐4 to 14‐crown‐4 to 15‐crown‐5 to 18‐crown‐6.