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A Novel Reaction of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) or 1,5‐Diazabicyclo[4.3.0]non‐5‐ene (DBN) with Benzyl Halides in the Presence of Water
Author(s) -
Shi Min,
Shen YuMei
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1355::aid-hlca1355>3.0.co;2-m
Subject(s) - chemistry , amide , halide , ene reaction , medicinal chemistry , lithium amide , organic chemistry , stereochemistry , catalysis , enantioselective synthesis
1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) reacted with benzyl halides in CH 2 Cl 2 /H 2 O 1 : 1 ( v / v ) to afford a mixture of eleven‐membered cyclic amide 1 and seven‐membered cyclic amide 2 . When the reaction was carried out in EtOH/H 2 O 1 : 1 ( v / v ), product 2 was obtained as the major product. 1,5‐Diazabicyclo[4.3.0]non‐5‐ene (DBN) gave the five‐membered cyclic amide 3 as the sole product under the same reaction conditions.