Imidazole → 1-(2-thienyl)-2-(1H-imidazol-1-yl)ethanone
Reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1>>[S:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:1](=[O:3])[CH2:2][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1Participants
Procedure
As illustrated in the following diagram, the thienyl compounds of this invention can be prepared by an initial bromination of 2-acetylthiophene 1, and reacting the resulting bromo derivative 2 with imidazole to produce the 1-(2-thienyl)-2-(1H-imidazol-1-yl)ethanone 3. Reaction of compound 3 with N-methylhyroxylamine hydrochloride provides the 1-(2-thienyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide 4 which is included in the subject matter of our co-pending application Ser. No. 900,856 filed Aug. 27, 1986 entitled "α-Substituted Ketonitrone Derivatives" whose disclosure is incorporated herein by reference. The nitrone compound 4 is then treated with styrene or an appropriate styrene (or allyl phenyl ether or alkyl phenyl thioether) derivative 5 to give a diastereomeric mixture of the desired cis- and trans-5-(phenyl, phenoxymethyl or phenylthiomethyl)-3-(2-thienyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine 6. ##STR3##
Sources & evidence
- ORD record
- ord-f4632600abbb4915a9c5958cf8f2931d
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04769470
Reaction notes
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