Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Download PDF
Synlett 2005(8): 1239-1242
DOI: 10.1055/s-2005-865235
DOI: 10.1055/s-2005-865235
LETTER
© Georg Thieme Verlag Stuttgart · New YorkInteresting Acid-Catalyzed O-N-Type Smiles Rearrangement Reactions of 2-Pyrimidinyloxy-N-Arylbenzylamine Derivatives
Further Information
Received
10 March 2005
Publication Date:
21 April 2005 (online)
Publication History
Publication Date:
21 April 2005 (online)
Abstract
The acid-catalyzed O-N-type Smiles rearrangement reactions of 2-pyrimidinyloxy-N-arylbenzylamine derivatives were investigated. The results show most 2-pyrimidinyloxy-N-arylbenzylamine derivatives can also undergo the Smiles rearrangement to the corresponding phenol derivatives in good yields at 25 °C in acetic acid-acetone (1:1).
Key words
Smiles rearrangement - acidic conditions - 2-pyrimidinyloxy-N-arylbenzylamine
- 1a
Warren LA.Smiles S. J. Chem. Soc. 1930, 956 - 1b
Warren LA.Smiles S. J. Chem. Soc. 1930, 1327 - 1c
Warren LA.Smiles S. J. Chem. Soc. 1931, 2207 - 2 Review:
Truce WE.Kreider EM.Brand WW. Org. React. 18: Wiley; New York: 1970. p.99MissingFormLabel - 3 Review:
Rádl S. Advances in Heterocyclic Chemistry 83: Academic Press; San Diego: 2002. p.189MissingFormLabel - For Smiles rearrangement, see:
- 4a
Weidner JJ.Weintraub PM. J. Heterocycl. Chem. 1997, 34: 1857 - 4b
Huber VJ.Bartsch RA. Tetrahedron 1998, 54: 9281 - 4c
Anelli PL.Brocchetta M.Calabi L.Secchi C.Uggeri F.Verona S. Tetrahedron 1997, 53: 11919 - 4d
Weidner JJ.Weintraub PM.Schnettler RA.Peet NP. Tetrahedron 1997, 53: 6303 - 4e
Proudfoot JR.Patel UR.Campbell SJ. J. Org. Chem. 1993, 58: 6996 - 5a
Lu L,Chen J,Cai X,Li MZ,Wu Y, andWang YH. inventors; Patent CN 1323788-A. ; Chem. Abstr. 2002, 137 74803MissingFormLabel - 5b
Lu L,Chen J,Wu J,Ling W,Mao LS,Li MZ,Cai X,Peng WL,Wu Y,Wu SG,Wang HJ,Wang GC,Cui H,Han SD,Qiu WL, andWang YH. inventors; World Patent WO 200234724-A1. ; Chem. Abstr. 2002, 136, 355244MissingFormLabel - 7
Wang H.-Y.Guo Y.-L.Lu L. J. Am. Soc. Mass Spectrom. 2004, 15: 1820 - For O-N-type Smiles rearrangement, see:
- 8a
Kleb KG. Angew. Chem., Int. Ed. Engl. 1968, 7: 291 - 8b
Selvakumar N.Srinivas D.Azhagan AM. Synthesis 2002, 2421 - For acid-catalyzed Smiles rearrangement, see:
- 9a
Rodig OR.Collier RE.Schlatzer RK. J. Org. Chem. 1964, 29: 2652 - 9b
Shin JM.Cho YM.Sachs G. J. Am. Chem. Soc. 2004, 126: 7800
References
Analytical data for these compounds are available upon request from the authors. Compounds 1a and 1c have been used in rape fields in China.