Proline-Catalyzed Simple and Efficient Synthesis of 1,8-Dioxo-decahydroacridines in Aqueous Ethanol Medium

REFERENCES

• Antman , E. ; Muller , J. ; Goldberg , S. ; Macalpin , R. ; Rubenfire , M. ; Tabatznik , B. ; Liang , C. ; Heupler , F. ; Achuff , S. ; Reichek , N. ; Geltman , E. ; Kerin , N. Z. ; Neff , R. K. ; Raunwald , E. Nifedipine therapy for coronary-artery spasm—Experience in 127 patients . N. Engl. J. Med. 1980 , 302 , 1269 – 1273 .
   PubMed Web of Science ®Google Scholar
• (a) Guazzi , M. ; Olivari , M. ; Polese , A. ; Fiorentini , C. ; Margrini , F. ; Moruzzi , P. Nifedipine, a new antihypertensive with rapid action . Clin. Pharmacol. Ther. 1977 , 22 , 528 – 532 ; (b) Hornung , R. S. ; Gould , B. A. ; Jones , R. I. ; Sonecha , T. N. ; Raferty , E. B. Nifedipine tablets for systemic hypertension: A study using continuous ambulatory intraarterial recording . Am. J. Cardiol. 1983 , 51 , 1323 – 1325 .
   PubMed Web of Science ®Google Scholar
• Delfourne , E. ; Roubin , C. ; Bastide , J. The first synthesis of the pentacyclic pyridoacridine marine alkaloids: Arnoamines A and B. J. Org. Chem. 2000, 65, 5476–5479.
   PubMed Web of Science ®Google Scholar
• Antonini , J. ; Polucci , P. ; Magnano , A. ; Martelli , S. Synthesis, antitumor cytotoxicity, and DNA binding of novel N-5,2-di(ω-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamides . J. Med. Chem. 2001 , 44 , 3329 – 3333 .
   PubMed Web of Science ®Google Scholar
• Ferlin , M. G. ; Marzano , C. ; Chiarelotto , G. ; Baccichetti , F. ; Bordin , F. Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives . Eur. J. Med. Chem. 2000 , 827 – 837 .
   PubMed Web of Science ®Google Scholar
• For MCR reviews, see (a) Weber , L. The application of multi-component reactions in drug discovery . Curr. Med. Chem . 2002 , 9 , 2085 – 2093 ; (b) Armstrong , R. W. ; Combs , A. P. ; Tempest , P. A. ; Brown , S. D. ; Keating , T.A. Multiple-component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. 1996 , 29 , 123 – 131 .
   PubMed Web of Science ®Google Scholar
• Lindstrőm , U. M. Stereoselective organic reactions in water . Chem. Rev . 2002 , 102 , 2751 – 2772 .
   PubMed Web of Science ®Google Scholar
• (a) Li , C. -J. ; Chan , T. -H. Organic Reactions in Aqueous Media ; Wiley : New York , 1997 ; (b) Grieco , P. A. Organic Synthesis in Water ; Blackie Academic and Professional : London , 1998 ; (c) Li, C. -J. Organic reactions in aqueous media—with a focus on carbon–carbon bond formations: A decade update. Chem. Rev. 2005, 105, 3095–3165; (d) Kobayashi, S.; Manabe, K. Development of novel lewis acid catalysts for selective organic reactions in aqueous media. Acc. Chem. Res. 2002, 35, 209–217 .
   Google Scholar
• Ribe , S. ; Wipf , P. Water-accelerated organic transformations . Chem. Commun. 2001 , 299 – 307 .
   Web of Science ®Google Scholar
• (a) List , B. Proline-catalyzed asymmetric reactions . Tetrahedron 2002 , 58 , 5573 – 5590 , and references cited therein; (b) Enders , D. ; Gasperi , T. Proline organocatalysis as a new tool for the asymmetric synthesis of ulosonic acid precursors . Chem. Commun. 2007 , 88 – 90 ; (c) Notz , W. ; Tanaka , F. ; Barbas , C. F. Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels–Alder reactions . Acc. Chem. Res. 2004 , 37 , 580 – 591 .
   Web of Science ®Google Scholar
• (a) Martin , N. ; Quinteiro , M. ; Seoane , C. ; Soto , L. ; Mora , A. ; Suarez , M. ; Ockoa , E. ; Morals , A. Synthesis of conformational study of acridine derivatives related to 1,4-dihydropyridines . J. Heterocyl. Chem. 1995 , 32 , 235 – 238 ; (b) Suarez , M. ; Loupy , A. ; Salfran , E. ; Moran , L. ; Rolando , E. Synthesis of decahydroacridines under microwaves using ammonium acetate supported on alumina . Heterocycles 1999 , 51 , 21 – 27 .
   Web of Science ®Google Scholar
• (a) Dabiri , M. ; Baghbanzadeh , M. ; Arzroomchilar , E. 1-Methylimidazolium trifluoroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxodecahydroacridines . Catal. Commun. 2008 , 9 , 939 – 942 ; (b) Das , B. ; Thirupathi , P. ; Mahender , I. ; Reddy , V. S. ; Rao , Y. K. Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines . J. Mol. Catal. A: Chem. 2006 , 247 , 233 – 239 ; (c) Jin , T. S. ; Zhang , J. S. ; Guo , T. T . ; Wang , A. Q. ; Li , T. S. One-pot clean synthesis of 1,8-dioxo-decahydroacridines catalyzed by p-dodecyl-benezenesulfonic acid in aqueous media . Synthesis 2004 , 2001 – 2005 ; (d) Wang , X. S. ; Shi , D. Q. ; Wang , S. H. ; Tu , S. J. Synthesis of 9-aryl-10-(4-methylphenyl)polyhydroacridine under microwave irradiation . Chin. J. Org. Chem. 2003 , 23 , 1291 – 1293 ; (e) Schekotikhin , Y. M. ; Getmanenko , Y. A. ; Nickolaeva , T. G. ; Kriven'ko , A. P. Synthesis of 9-R1-10-R-1,8-dioxodecahydroacridines and dioximes on their basis . Khim. Geterotsikl. Soedin. 2001 , 10 , 1344 – 1349 .
   Web of Science ®Google Scholar
• Palimkar , S. S. ; Siddiqui , S. A. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. Ionic liquid-promoted regiospecific friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines. J. Org. Chem. 2003, 68, 9371–9378.
   PubMed Web of Science ®Google Scholar
• Gholap , A. R. ; Venkatesan , K. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. Ionic liquid–promoted novel and efficient one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature under ultrasound irradiation . Green Chem . 2004 , 3 , 147 – 150 .
   Web of Science ®Google Scholar
• Potewar , T. M. ; Lahoti , R. J. ; Daniel , T. ; Srinivasan , K. V. Efficient synthesis of 3,5,6-trisubstituted-1,2,4-triazines in the Brønsted acidic ionic liquid, 1-n-butylimidazolium tetrafluoroborate ([Hbim]BF4) . Synth. Commun. 2007 , 37 , 261 – 269 .
   Web of Science ®Google Scholar