Stollé synthesis

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The Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides (or oxalyl chloride).[1][2][3][4]

The Stollé synthesis

The first step is an amide coupling, while the second step is a Friedel–Crafts reaction.[5][6] An improved procedure has been developed.[7][8]

References[edit]

  1. ^ Stollé, R. Ber. (1913). "Über eine neue Methode zur DarstellungN-substituierter Isatine. (Vorläufige Mitteilung)". Berichte der deutschen chemischen Gesellschaft 46 (3): 3915. doi:10.1002/cber.191304603186. 
  2. ^ Stollé, R. (1914). "Über Phenyl-oxindol". Ber. 47 (2): 2120. doi:10.1002/cber.191404702112. 
  3. ^ Stollé, R. (1923). "Über N-substituierte Oxindole und Isatine". J. Prakt. Chem. 105: 137. doi:10.1002/prac.19221050111.  |first2= missing |last2= in Authors list (help); |first3= missing |last3= in Authors list (help); |first4= missing |last4= in Authors list (help); |first5= missing |last5= in Authors list (help)
  4. ^ Stollé, R. (1930). "Über N-substituierte Oxindole und Isatine". J. Prakt. Chem. 128: 1. doi:10.1002/prac.19301280101.  |first2= missing |last2= in Authors list (help); |first3= missing |last3= in Authors list (help); |first4= missing |last4= in Authors list (help); |first5= missing |last5= in Authors list (help)
  5. ^ Sumpter, W. C. (1944). "The Chemistry of Isatin". Chem. Rev. 34 (3): 396. doi:10.1021/cr60109a003. 
  6. ^ Sumpter, W. C. (1945). "The Chemistry of Oxindole". Chem. Rev. 37 (3): 443–479. doi:10.1021/cr60118a003. 
  7. ^ Julian; Pikl (1935). "Studies in the Indole Series. IV. The Synthesis of d,l-Eserethole". J. Am. Chem. Soc. 57 (3): 563. doi:10.1021/ja01306a053. 
  8. ^ Rutenberg, M. W.; Horning, E. C. (1963), "1-Methyl-3-ethyloxindole", Org. Synth. ; Coll. Vol. 4: 620 

See also[edit]