Dimroth Rearrangement

O. Dimroth, Ann. 364, 183 (1909); 459, 39 (1927).

Rearrangement whereby exo- and endocyclic heteroatoms on a heterocyclic ring are translocated:



D. J. Brown, J. S. Harper in Pteridine Chemistry, W. Pfleiderer, E. C. Taylor, Ed. (Macmillan, New York, 1964) pp 219-230; D. J. Brown in Mechanisms of Molecular Migrations vol. 1, B. S. Thyagarajan, Ed. (Wiley-Interscience, New York, 1968) p 209; D. J. Brown in The s Suppl. I (Interscience, New York, 1970) p 287; D. J. Brown, K. Lenega, J. Chem. Soc. Perkin Trans. I 1974, 372. Mechanism: K. Vaughan et al., Heterocyclic Chem. 28, 1709 (1991); T. Itaya et al., Chem. Pharm. Bull. 45, 832 (1997). Modified reaction: A. R. Katritzky et al., J. Org. Chem. 57, 190 (1992); A. R. Pagano et al., J. Org. Chem. 63, 3213 (1998). Review: E. S. H. El Ashry et al., Adv. Heterocyclic Chem. 75, 79-167 (2000).