Observation of O→N type smiles rearrangement in certain alkyl aryl nitro compounds

Synthesis

Volumn , Issue 16, 2002, Pages 2421-2425

  Selvakumar, Natesan ^a   Srinivas, Deekonda ^a   Azhagan, Azagarsamy Malar ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Cyclization; Isomerization; Nitro compound; Nucleophilic addition; Rearrangement

Indexed keywords

CHEMICAL ANALYSIS; OXYGEN; SYNTHESIS (CHEMICAL);

NUCLEOPHILES;

NITROGEN COMPOUNDS;

NITRO DERIVATIVE; OXYGEN;

ARTICLE; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0036437607     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35227     Document Type: Article

References (14)

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9. For example see: Cao, B.; Park, H.; Joullie, M. M. J. Am. Chem. Soc. 2002, 124, 520; during the preparation of the compound 26 the authors report the formation of an unidentified aryl amine. We believe that the undesired aryl amine is presumably the structure 28 a product of Smiles rearrangement via the, intermediate 27 (Figure 2).
10. Bischofberger, N.; Waldmann, H.; Saito, T.; Simon, E. S.; Lees, W.; Bednarski, M. D.; Whitesides, G. M. J. Org. Chem. 1988, 53, 3457.
11. Similar studies on primary acyclic amines have been reported although under different conditions: (a) Knipe, A. C.; Sridhar, N. Synthesis 1976, 606. (b) Mutai, K.; Kobayashi, K. Bull. Chem. Soc. Jpn. 1981, 54, 462.
12. Similar studies on primary acyclic amines have been reported although under different conditions: (a) Knipe, A. C.; Sridhar, N. Synthesis 1976, 606. (b) Mutai, K.; Kobayashi, K. Bull. Chem. Soc. Jpn. 1981, 54, 462.
13. A similar amino-ethanol substrate undergoing Smiles rearrangement in a polyfunctional vinylthiohalobenzene substrate has been reported: (a) Amosova, S. V.; Gostevsgaya, V. I.; Gavrilova, G. M.; Afonin, A. V.; Toryashinova, D. D. Zh. Org. Khim. 1993, 29, 2416. (b) Yilmaz, I.; Shine, H. J. Gazz. Chim. Ital. 1989, 119.
14. A similar amino-ethanol substrate undergoing Smiles rearrangement in a polyfunctional vinylthiohalobenzene substrate has been reported: (a) Amosova, S. V.; Gostevsgaya, V. I.; Gavrilova, G. M.; Afonin, A. V.; Toryashinova, D. D. Zh. Org. Khim. 1993, 29, 2416. (b) Yilmaz, I.; Shine, H. J. Gazz. Chim. Ital. 1989, 119.