Clean Procedure for Synthesis of Chromeno[4,3‐b]benzo [f]quinolin‐6‐one Derivatives: Reaction of N‐arylidenenaphthalen‐2‐amine with 4‐Hydroxycoumarin in Aqueous Media

Abstract A short and simple synthesis of chromeno[4,3‐b]benzo[f]quinolin‐6‐one derivatives was accomplished in good to high yields via the reaction of N‐arylidenenaphthalen‐2‐amine with 4‐hydroxycoumarin in aqueous media catalyzed by TEBAC. The structures were established by spectroscopic data and further confirmed by X‐ray analysis. In addition, water was chosen as a green solvent.

[1]  Xianyong Wei,et al.  A Clean Synthesis of 1‐Oxo‐hexahydroxanthene Derivatives in Aqueous Media Catalyzed by TEBA , 2005 .

[2]  D. Shi,et al.  Synthesis of 4H,5H-pyrano[3,2-c][1]benzopyran-5-ones in aqueous media , 2004 .

[3]  S. Banerjee,et al.  One-Pot Synthesis of 2-Alkyl/Arylamino-4-oxo-4H-1-Benzopyran-3-Carboxaldehyde from 4-oxo-4H-1-Benzopyran-3-Carboxaldehyde , 2003 .

[4]  M. Chiarini,et al.  A New Green Approach to the Friedländer Synthesis of Quinolines , 2003 .

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

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

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

[8]  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.

[9]  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.

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

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

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

[13]  R. Martínez,et al.  Reaction of β‐arylidennaphthylamines with 4‐hydroxycoumarin. A correction in structural assignment of the product. III , 1990 .

[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]  M. H. Elnagdi,et al.  Nitriles in heterocyclic synthesis: novel synsthesis of benzo[c]-coumarin and of benzo[c]pyrano[3,2-c]quinoline derivatives , 1987 .

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

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

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

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

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