Tandem [4+2] cycloaddition versus electrocyclisation reactions of 1-aryl-2-phenyl-5-alkyl/aryl-1,3-diazapenta-1,3,4-trienes in aza-Wittig reactions of N′-aryl-N-(triphenylphosphoranlidene) benzenecarboximidamides with ketenes
✍ Scribed by S Jayakumar; Vipan Kumar; Mohinder P Mahajan
- Book ID
- 104230197
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 66 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
1-Aryl-2-phenyl-5-alkyl/aryl-1,3-diazapenta-1,3,4-triene 3 generated in situ aza-Wittig reactions of N%-aryl-N-(triphenylphosphoranylidene)carboximidamides 1 which are shown to undergo selective [4+2] cycloaddition and electrocyclisation reactions leading to the formation of novel pyrimidinone derivatives 5 and quinazoline derivatives 7 with monosubstituted ketenes and diphenylketene, respectively.
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## Abstract The reaction of (E)‐3‐aryl‐2‐propenoic acid derivatives with (N‐isocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2‐[(E)‐2‐aryl‐1‐ethenyl]‐1,3,4‐oxadiazole via an intramolecular aza‐Wittig reaction in good yields under neutral condition
The tandem 1,3 cycloaddition-rearrangement and open chain reactions of 2-aryl-N-aroyl-4,5-dimethyl-1,2,3-triazol-1-imines with DMAD at room temperature and in refluxing toluene are described.