Diammonium Hydrogen Phosphate: An Efficient and Versatile Catalyst for the One‐Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media

References

• Anastas , P. T. and Williamson , T. C. 1996 . Green Chemistry, Designing Chemistry for the Environment Edited by: Anastas , P. T. and Williamson , T. C. 1 Washington DC : American Chemical Society .
   Google Scholar
• Grieco , P. A. 1998 . Organic Synthesis in Water 1 – 278 . London : Thomson Science .
   Google Scholar
• Li , C.‐J. 2005 . Asymmetric reaction cascades in aqueous media . Chem. Rev. , 105 : 3095 – 3165 .
   PubMed Web of Science ®Google Scholar
• Green , G. R. , Evans , J. M. and Vong , A. K. 1995 . Comprehensive Heterocyclic Chemistry II Edited by: Katritzky , A. R. , Rees , C. W. and Scriven , E. F.V. Vol. 5 , 469 – 490 . Oxford : Pergamon Press .
   Google Scholar
• Foye , W. O. 1991 . “ Prinicipi di Chemico Farmaceutica Piccin ” . 416 Padova, , Italy
   Google Scholar
• Andreani , L. L. and Lapi , E. 1960 . On some new esters of coumarin‐3‐carboxylic acid with balsamic and bronchodilator action . Bull. Chim. Farm. , 99 : 583 – 586 .
   PubMedGoogle Scholar
• Zhang , Y. L. , Chen , B. Z. , Zheng , K. Q. , Xu , M. L. and Lei , X. H. 1982 . Chemotherapeutic studies on schistosomiasis, XXV: Derivatives of substituted coumarin‐3‐carboxylic esters and amides . Yao Xue Xue Bao , 17 : 17 – 22 . Chem. Abstr. 1982 96, 135383e
   PubMedGoogle Scholar
• Bonsignore , L. , Loy , G. , Secci , D. and Calignano , A. 1993 . Synthesis and pharmacological activaty of 2‐oxo‐(2H)‐1‐benzopyran‐3‐carboxamide derivatives . Eur. J. Med. Chem. , 28 : 517 – 520 .
   Web of Science ®Google Scholar
• Witte , E. C. , Neubert , P. and Roesch , A. 1986 . Synthesis of new 2H‐benzopyrzn‐2‐one derivatives . Chem. Abstr. , 104 : 224915f Ger. Offen DE. 3427985
   Google Scholar
• Konkoy , C. S. , Fick , D. B. , Cai , S. X. , Lan , N. C. and Keana , J. F. W. 2001 . Substituted 5‐oxo‐ 5,6,7,8‐tetrahydro‐4H‐1‐benzopyrans and benzothiopyrans and the use thereof as potentiators of ampa . Chem. Abstr. , 134 : 29313a PCT Int. Appl. WO 75 123, 2000
   Google Scholar
• Hatakeyama , S. , Ochi , N. , Numata , H. and Takano , S. 1988 . A new route to substituted 3‐methoxycarbonyldihyropyrans . J. Chem. Soc., Chem. Commun. , : 1202 – 1204 .
   Google Scholar
• Cingolani , G. M. , Gualtieri , F. and Pigini , M. 1969 . Researches in the field of antivirial compounds: Manich bases of 3‐hydrroxycoumarin . J. Med. Chem. , 12 : 531 – 532 .
   PubMed Web of Science ®Google Scholar
• Arnesto , D. , Horspool , W. M. , Martin , N. , Ramos , A. and Seaone , C. 1989 . Synthesis of cyclobutenes by the novel photochemical ring contraction of 4‐substituted 2‐amino‐3,5‐dicyano‐6‐phenyl‐4H‐pyrans . J. Org. Chem. , 54 : 3069 – 3072 .
   Web of Science ®Google Scholar
• Singh , K. , Singh , J. and Singh , H. 1996 . A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3‐oxazinanes and oxazolidines with carbon nucleophiles . Tetrahedron , 52 : 14273 – 14280 .
   Web of Science ®Google Scholar
• Wang , X. S. , Shi , D. Q. , Tu , S. T. and Yao , C. S. 2003 . A convenient synthesis of 5‐oxo‐5,6,7,8‐tetrahydro‐4H‐benzo‐[b]‐pyran derivatives catalyzed by KF‐alumina . Synth. Commun. , 33 : 119 – 126 .
   Web of Science ®Google Scholar
• Tu , S. J. , Gao , Y. , Guo , C. , Shi , D. and Lu , Z. 2002 . A convenient synthesis of 2‐amino‐5,6,7,8‐tetrahydro‐5‐oxo‐4‐aryl‐7,7‐dimethyl‐4H‐benzo‐[b]pyran‐3‐carbonitrile under microwave irradiation . Synth. Commun. , 32 : 2137 – 2141 .
   Web of Science ®Google Scholar
• Li , J. T. , Xu , W. Z. , Yang , L. C. and Li , T. S. 2004 . One‐pot synthesis of 2‐amino‐4‐aryl‐3‐carbalkoxy‐7,7‐dimethyl‐5,6,7,8‐tetrahydrobenzo[b]pyran derivatives catalyzed by KF/basic Al2O3 under ultrasound irradiation . Synth. Commun. , 34 : 4565 – 4571 .
   Web of Science ®Google Scholar
• Kaupp , G. , Naimi‐Jamal , M. R. and Schmeyers , J. 2003 . Solvent‐free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield . Tetrahedron , 59 : 3753 – 3760 .
   Web of Science ®Google Scholar
• Fan , X. , Hu , X. , Zhang , X. and Wang , J. 2004 . Ionic liquid promoted Knoevenagel and Michael reactions . Aus. J. Chem. , 57 : 1067 – 71 .
   Google Scholar
• Jin , T. S. , Wang , A. Q. , Wang , X. , Zhang , J. S. and Li , T. S. 2004 . A clean one‐pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyle ammonium bromide in aqueous media . Synlett , : 871 – 873 .
   Google Scholar
• Tu , S. J. , Wang , H. , Feng , J. Q. , Tang , A. L. and Feng , G. C. 2001 . A convenient synthesis of 2‐amino‐5,6,7,8‐tetrahydro‐5‐oxo‐4‐aryl‐7,7‐dimethyl‐4H‐benzo[b]pyran3‐ethylcarboxylates.under microwave irradiation . Synth. Commun. , 31 : 2663 – 2666 .
   Web of Science ®Google Scholar
• Devi , I. and Bhuyan , P. J. 2004 . Sodium bromide–catalysed one‐pot synthesis of tetrahydrobenzo[b]pyrans via a three‐component cyclocondensation under microwave irradiation and solvent‐free conditions . Tetrahedron Lett. , 45 : 8625 – 8627 .
   Web of Science ®Google Scholar
• Lewis , R. J. Sr . 1997 . Hawley's Condensed Chemical Dictionary , 13 Ed. New York : Von Nostrand Reinhold .
   Google Scholar
• 1980 . Kirk‐Othmer Encyclopedia of Chemical Technology , 3rd ed. Vol. 10 , 93 – 97 . New York
   Google Scholar
• Büchner , W. , Schliebs , R. , Winter , G. and Büchel , K. H. 1989 . Industrial Inorganic Chemistry 189 – 197 . Weinheim : VCH Verlag .
   Google Scholar
• 1987 . Ullmann's Encyclopedia of Industrial Chemistry Vol. A10 , 353 – 357 . 377 Weinheim : VCH Verlag .
   Google Scholar
• Salehi , P. , Dabiri , M. , Khosropour , A. R. and Roozbehniya , P. 2006 . Diammonium hydrogen phosphate: A versatile and cheap reagent for one pot synthesis of dihydropyrimidinones, quinazolinones and azalactones under solvent free conditions . J. Iranian Chem. Soc. , 3 : 98 – 105 .
   Web of Science ®Google Scholar
• Balalaie , S. , Bararajanian , M. , Hekmat , S. and Salehi , P. 2006 . A novel and efficient and green procedure for the Knoevenagel condensation catalyzed by dammonium hydrogen phosphate in water . Synth. Commun. , 36 : 2549 – 2557 .
   Web of Science ®Google Scholar
• Balalaie , S. , Hashtroudi , M. S. and Sharifi , A. 1999 . Microwave‐assisted synthesis of triazones and 4‐oxo‐oxadiazinane in dry media . J. Chem. Res Synop. , : 392 – 393 .
   Google Scholar
• Balalaie , S. , Arabanian , A. and Hashtroudi , M. S. 2000 . Zeolite HY and silica gel as new and efficient heterogenous catalysts for the synthesis of triarylimidazoles under microwave irradiation . Monatsh. Chem. , 131 : 945 – 948 .
   Web of Science ®Google Scholar
• Balalaie , S. and Arabanian , A. 2000 . One‐pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation . Green Chem. , 2 : 274 – 276 .
   Web of Science ®Google Scholar
• Balalaie , S. and Kowsari , E. 2001 . One‐pot synthesis of N‐substituted 4‐aryl‐1,4‐dihydropyridines under solvent‐free conditions and microwave irradiation . Monatsh. Chem. , 132 : 1551 – 1555 .
   Google Scholar
• Balalaie , S. , Kowsari , E. and Hashtroudi , M. S. 2003 . An efficient method for the synthesis of 3‐cyano‐6‐hydroxy‐2(1H0)‐pyridinones under microwave irradiation and solvent‐free conditions . Monatsh. Chem. , 134 : 453 – 456 .
   Google Scholar
• Balalaie , S. , Hashemi , M. M. and Akhbari , M. 2003 . A novel one‐pot synthesis of tetrasubstituted imidazoles under solvent‐free conditions and microwave irradiation . Tetrahedron Lett. , 44 : 1709 – 1711 .
   Web of Science ®Google Scholar
• Balalaie , S. , Soleiman‐Beigi , M. and Rominger , F. 2005 . Novel one‐pot synthesis of new derivatives of dihydropyrimidinones, unusal multisubstituted imidazoline‐2‐ones: X‐ray crystallography structure . J. Iranian Chem. Soc. , 2 : 319 – 329 .
   Web of Science ®Google Scholar
• Balalaie , S. , Bararjanian , M. , Amani , M. A. and Movassagh , B. 2006 . (s)‐Proline as a neutral and efficient catalyst for the one‐pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media . Synlett , : 263 – 266 .
   Web of Science ®Google Scholar
• Balalaie , S. , Bararjanian , M. and Rominger , F. 2006 . An efficient one‐pot synthesis of 6‐aryl‐5‐cyano‐2‐thiopyrimidinone derivatives and their piperidinium ionic forms, X‐ray crystal structures . J. Heterocycl Chem. , 43 : 821 – 826 .
   Web of Science ®Google Scholar