Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction

E-mail: keum@korea.ac.krReceived January 14, 2013, Accepted February 22, 2013Key Words : Triarylmethane, Malachite green, Carbinol, Michael-type addition, α,β-unsaturated iminium saltsTriarylmethane (TAM) compounds, also known as “leuco-TAM” (LTAM), are used in a variety of chemical, pharma-ceutical, and life science industries, including thermal imag-ing and carbonless copying materials.

[1]  S. Keum,et al.  Novel dimeric leuco-TAM dyes, 1,4-bis{(1E,3Z)-1,3-bis(1,3,3-trimethylindolin-2-ylidene)propan-2-yl}benzene derivatives: Structure and spectroscopic characterization , 2012 .

[2]  Min-Hyung Lee,et al.  Novel unsymmetrical leuco-TAM, (2E, 2′E)-2,2′-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives: Synthesis and structure elucidation , 2011 .

[3]  A. Cho,et al.  Diastereomeric isomerization of hetaryl leuco-TAM dyes, (2Z, 2'E)-2,2'-(2-phenyl propane-1,3-diylidene)bis(1,3,3-trimethylindoline) derivatives in various organic solvents , 2010 .

[4]  F. Sauriol,et al.  1H and 13C NMR assignments for new heterocyclic TAM leuco dyes, (2Z,2′E)‐2,2′‐(2‐phenyl propane‐1,3‐diylidene) bis(1,3,3‐trimethylindoline) derivatives. Part II , 2008, Magnetic resonance in chemistry : MRC.

[5]  Sujit Roy,et al.  Dual-reagent catalysis within Ir-Sn domain: highly selective alkylation of arenes and heteroarenes with aromatic aldehydes. , 2007, The Journal of organic chemistry.

[6]  E. Klemm,et al.  Novel Polyarylene−Triarylmethane Dye Copolymers , 2006 .

[7]  V. Nair,et al.  Recent Advances in the Chemistry of Triaryl- and Triheteroarylmethanes , 2006 .

[8]  V. Nair,et al.  Practical synthesis of triaryl- and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride. , 2005, Organic letters.

[9]  Shivaji Srivastava,et al.  Toxicological effects of malachite green. , 2004, Aquatic toxicology.

[10]  S. J. Culp,et al.  Synthesis and characterization of N-demethylated metabolites of malachite green and leucomalachite green. , 2003, Chemical research in toxicology.

[11]  G. Indig,et al.  Effect of molecular structure on the selective phototoxicity of triarylmethane dyes towards tumor cells , 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[12]  D. A. Dougherty,et al.  The Cationminus signpi Interaction. , 1997, Chemical reviews.

[13]  D. Alderman Malachite green: a review , 1985 .

[14]  S. Keum,et al.  X-ray Crystal Structure of Hetaryl Leuco-TAM Dyes, (2Z,2'E)-2,2'-(2-Phenyl Propane-1,3-diylidene) Bis(1,3,3-trimethyl indoline) Derivatives , 2009 .

[15]  M. Nichols,et al.  Effect of molecular structure on the performance of triarylmethane dyes as therapeutic agents for photochemical purging of autologous bone marrow grafts from residual tumor cells. , 2000, Journal of pharmaceutical sciences.

[16]  S. Godtfredsen,et al.  Ullmann ' s Encyclopedia of Industrial Chemistry , 2017 .

[17]  P. Hodge,et al.  Protective groups in organic synthesis , 1981 .