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

References

• Hajela , K. and Kapil , R. S. 1997 . Synthesis and post‐coital contraceptive activity of a new series of substituted 2,3‐diaryl‐ 2H‐1‐benzopyrans . European J. Med. Chem. , 32 : 135
   Web of Science ®Google Scholar
• Rovnyak , G. C. , Ahmed , S. Z. , Baird , A. J. , Ding , C. Z. , Dzwonczyk , S. , Ferrata , F. N. and Humphreys , W. G. 1997 . Cardioselective antiischemic ATP‐sensitive potassium channel (KATP) openers. 5. Identification of 4‐(N‐Aryl)‐substituted benzopyran derivatives with high selectivity . J. Med. Chem. , 40 : 24
   PubMed Web of Science ®Google Scholar
• Chen , M. J. , Lee , Y. M. , Sheu , J. R. , Hu , C. T. and Yen , M. H. 1998 . ATP‐sensitive potassium‐channel‐opening activity of CL‐065, a 3‐[(substituted‐carbonyl)amino]‐ 2H‐1‐benzopyran, in the rat . J. Phar. Pharmacol. , 50 : 83
   Google Scholar
• Horino , H. , Mimura , T. , Kagechika , K. , Ohta , M. , Kubo , H. and Kitagawa , M. 1998 . Synthesis and antihypertensive activity of 4‐(diazabicyclo[4.1.0]heptenyloxy)benzopyran derivatives and their analogs . Chem. Pharm. Bull , 46 : 602
   PubMedGoogle Scholar
• Mannhold , R. , Cruciani , G. , Weber , H. , Lemoine , H. , Derix , A. , Weichel , C. and Clementi , M. 1999 . 6‐Substituted benzopyrans as potassium channel activators: synthesis, vasodilator properties, and multivariate analysis J . Med. Chem. , 42 : 981
   Google Scholar
• Sun , H. B. , Chen , W. Y. , Peng , S. X. , Wang , T. and Liu , G. Q. 1997 . 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 . Gaodeng Xuexiao Huaxue Xuebao , 18 : 730
   Google Scholar
• Kossakowski , J. , Jerzy , Z. T. and Suski , S. 1998 . Synthesis of aminopropanol derivatives of 7‐ethoxy‐8‐hydroxy‐ and 6,7‐diethoxy‐8‐hydroxy‐2H‐1‐benzopyran‐2‐one with an expectedb‐adrenolytic activity . Acta Pol. Pharma , 55 : 77
   Google Scholar
• El‐Shaaer , H. M. , Foltinova , P. , Lacova , M. , Chovancova , J. and Stankovicova , H. 1998 . Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4‐oxo‐4H‐benzopyran‐3‐carboxaldehydes with aminobenzothiazoles and hydrazides . Farmaco , 53 : 224
   PubMedGoogle Scholar
• Johnson , A. T. , Wang , L. , Standeven , A. M. , Escobar , M. and Chandraratna , R. A. S. 1999 . Synthesis and biological activity of high‐affinity retinoic acid receptor antagonists . Bio. Med. Chem , 7 : 1321
   PubMedGoogle Scholar
• Li , C. J. 1993 . Organic reaction in aqueous media with a focus on carbon‐carbon bond formation . Chem. Rev. , 93 : 2023
   Web of Science ®Google Scholar
• Fringuelli , F. , Piematti , O. , Pizzo , F. and Vaccaro , L. 2001 . Recent advances in Lewis acid catalyzed Diels‐Alder reactions in aqueous media . Eur. J. Org. Chem. , : 439
   Google Scholar
• Breslow , R. and Rideout , D. C. 1980 . Hydrophobic acceleration of Diels‐Alder reactions . J. Am. Chem. Soc. , 102 : 7816
   Web of Science ®Google Scholar
• Breslow , R. 1991 . Hydrophobic effects on simple organic reactions in water . Acc. Chem. Res. , 24 : 159
   Web of Science ®Google Scholar
• Breslow , R. , Maitra , U. and Rideout , D. C. 1983 . Selective Diels‐Alder reactions in aqueous solutions and suspensions . Tetrahedron Lett. , 24 : 1901
   Web of Science ®Google Scholar
• Breslow , R. and Maitra , U. 1984 . On the origin of product selectivity in aqueous Diels‐Alder reactions . Tetrahedron Lett. , 25 : 1239
   Web of Science ®Google Scholar
• Ponaras , A. A. 1983 . A new variant of the claisen rearrangement capable of creating the bond between two quaternary centers . J. Org. Chem. , 48 : 3866
   Web of Science ®Google Scholar
• Coates , R. M. , Rogers , B. D. , Hobbs , S. J. , Peck , D. R. and Curran , D. P. 1987 . Synthesis and claisen rearrangement of alkoxyallyl enol ethers. Evidence for a dipolar transition state . J. Am. Chem. Soc , 109 : 1160
   Google Scholar
• Mattes , H. and Benezra , C. 1985 . Reformatsky‐type reactions in aqueous media use of bromomethyl‐acrylic acid for the synthesis of α‐methylene‐γ‐butyrolactones . Tetrahedron Lett. , 26 : 5697
   Web of Science ®Google Scholar
• Zhou , J. Y. , Lu , G. D. and Wu , S. H. 1992 . A new approach for the synthesis of α‐methylene‐γ‐butyrolactones from α‐bromomethylacrylic acid (or esters) . Synth. Commun. , 22 : 481
   Web of Science ®Google Scholar
• Delair , P. and Luche , J. L. 1989 . A new sonochemical carbonyl cross‐coupling reaction . J. Chem. Soc. Chem. Commun , : 398
   Google Scholar
• Shi , D. Q. , Zhuang , Q. Y. , Chen , J. , Wang , X. S. , Tu , S. J. and Hu , H. W. 2003 . Reaction of aromatic aldehydes with 5,5‐dimethyl‐1,3‐cyclohexandione in water . Chin. J. Org. Chem. , 23 : 694
   Web of Science ®Google Scholar
• Shi , D. Q. , Zhang , S. , Zhuang , Q. Y. , Wang , X. S. , Tu , S. J. and Hu , H. W. 2003 . Clean synthesis in water: darzens condensation reaction of aromatic aldehydes with phenacyl chloride . Chinese J. Chem. , 21 : 680
   Google Scholar
• Zhang , S. , Chen , J. , Shi , D. Q. , Zhuang , Q. Y. and Zhang , X. Q. 2003 . The condensation of aromatic aldehyde with active methylene compounds in water . J. of Xuzhou Normal Uni. , 21 : 42
   Google Scholar
• Wang , X. S. , Shi , D. Q. , Zhang , Y. F. , Wang , S. H. and Tu , S. J. 2004 . Synthesis of 9‐arylpolyhydroacridine in water catalyzed by triethylbenzylammonium chloride (TEBA) . Chin. J. Org. Chem. , 24 : 430
   Web of Science ®Google Scholar
• Wang , S. H. , Shi , D. Q. , Tu , S. J. and Wang , Y. C. 1999 . Studies on the uncatalyzed reactions of O‐substituted aromatic aldehydes with 5,5‐dimethyl‐1,3‐cyclohexandione . Chin. J. Org. Chem. , 19 : 483
   Google Scholar