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Novel synthesis of 5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones via the rhodium(II)-mediated Wolff rearrangement of 3-(thieno-2-yl)-3-oxo-2-diazopropanoates
- Issue Date
- Mar-2002
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.4, no.6, pp 873 - 876
- Pages
- 4
- Journal Title
- ORGANIC LETTERS
- Volume
- 4
- Number
- 6
- Start Page
- 873
- End Page
- 876
- ISSN
- 1523-7060
1523-7052
- Abstract
- [GRAPHICS] Treatment of thioaryolketene S,N-acetals 12 with Hg(OAc)(2) followed by addition of 2-diazo-3-trimethylsilyloxy-3-butenoic acid alkyl esters 15 in CH2Cl2 at room temperature gave 3-(3-alkylamino-5-arylthieno-2-yl)-3-oxo-2-diazopropanoates 16 in good yields. Subsequent reactions of 16 with a catalytic amount of Rh-2(OAc)(4).2H(2)O in benzene at reflux afforded a mixture of 5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 18 and the corresponding enols 19 in excellent yields.
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