A Clean Synthesis of 1‐Oxo‐hexahydroxanthene Derivatives in Aqueous Media Catalyzed by TEBA

Abstract A series of 1‐oxo‐1,2,3,4,9,10‐hexahydroxanthene derivatives were synthesized from substituted salicylaldehydes and substituted 1,3‐hexanedione in water at 90°C catalyzed by TEBA. The structure of the product was confirmed by X‐ray analysis. Compared with other synthetic methods, this new method has the advantages of easier workup, milder reaction conditions, high yields (85 ∼ 95%) and environmentally benign procedure.

[1]  S. Da.  The Condensation of Aromatic Aldehyde with Active Methylene Compounds in Water , 2003 .

[2]  O. Piermatti,et al.  Recent Advances in Lewis Acid Catalyzed Diels−Alder Reactions in Aqueous Media , 2001 .

[3]  R. Chandraratna,et al.  Synthesis and biological activity of high-affinity retinoic acid receptor antagonists. , 1999, Bioorganic & medicinal chemistry.

[4]  R. Mannhold,et al.  6-Substituted benzopyrans as potassium channel activators: synthesis, vasodilator properties, and multivariate analysis. , 1999, Journal of medicinal chemistry.

[5]  M. Ohta,et al.  Synthesis and antihypertensive activity of 4-(diazabicyclo[4.1.0]-heptenyloxy)benzopyran derivatives and their analogues. , 1998, Chemical & pharmaceutical bulletin.

[6]  H. Stankovičová,et al.  Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides. , 1998, Farmaco.

[7]  J. Sheu,et al.  Biochemical Pharmacology: ATP‐sensitive Potassium‐channel‐opening Activity of CL‐065, a 3‐[(Substituted‐carbonyl)amino]‐2H‐1‐benzopyran, in the Rat , 1998, The Journal of pharmacy and pharmacology.

[8]  W. Humphreys,et al.  Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity. , 1997, Journal of medicinal chemistry.

[9]  K. Hajela,et al.  Synthesis and post-coital contraceptive activity of a new series of substituted 2,3-diaryl-2H-1-benzopyrans , 1997 .

[10]  Sun Hong.  Studies on Potassium Channel Openers(I)─Synthesis and Cardiovascular Activity of Substituted trans-4-Amino-3, 4-dihydro-2, 2-dimethyl-2H-1-benzopyran-3-ols , 1997 .

[11]  Chao-Jun Li.  Organic reactions in aqueous media - with a focus on carbon-carbon bond formation , 1993 .

[12]  Jingyao Zhou,et al.  A New Approach for the Synthesis of α-Methylene-γ-Butyrolactones from α-Bromomethyl Acrylic Acids (or Esters) , 1992 .

[13]  Ronald Breslow,et al.  Hydrophobic Effects on Simple Organic Reactions in Water , 1991 .

[14]  J. Luche,et al.  A new sonochemical carbonyl cross-coupling reaction , 1989 .

[15]  B. D. Rogers,et al.  Synthesis and Claisen rearrangement of alkoxyallyl enol ethers. Evidence for a dipolar transition state , 1987 .

[16]  C. Benezra,et al.  Reformatsky-type reactions in aqueous media. Use ofbronometryl-acrylic acid for the synthesis of α-methylene-γ-butyrolactones. , 1985 .

[17]  R. Breslow,et al.  On the origin of product selectivity in aqueous diels-alder reactions , 1984 .

[18]  A. A. Ponaras.  A new variant of the claisen rearrangement capable of creating the bond between two quaternary centers , 1983 .

[19]  D. Rideout,et al.  Selective diels-alder reactions in aqueous solutions and suspensions , 1983 .

[20]  Ronald Breslow,et al.  Hydrophobic acceleration of Diels-Alder reactions , 1980 .