Recyclization of 2-Iminochromenes via Ketene Aminal Intermediates: One-Pot, Three-Component Reaction for Synthesis of 1,4-Dihydropyridines-fused-1,3-diazaheterocycles

REFERENCES

• (a) Mai , A. ; Valente , S. ; Meade , S. ; Carafa , V. ; Tardugno , M. ; Nebbisso , A. ; Galmozzi , A. ; Mitro , N. ; Fabiani , E. D. ; Altucci , L. ; Kazantsev , A. Study of 1,4-dihydropyridine structural scaffold: Discovery of novel sirtuin activators and inhibitors . J. Med. Chem. 2009 , 52 , 5496 ; (b) Fassihi , A. ; Azadpour , Z. ; Delbari , N. ; Saghaie , L. ; Memarian , H. R. ; Sabet , R. ; Alborzi , A. ; Miri , R. ; Pourabbas , B. ; Mardaneh , J. ; Mousavi , P. ; Moeinifard , B. ; Sadeghi-aliabadi , H. Synthesis and antitubercula reactivity of novel 4-substituted imidazolyl-2,6-dimethyl-N 3, N 5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides . Eur. J. Med. Chem. 2009 , 44 , 3253 ; (c) Cateni , F. ; Zacchigna , M. ; Pedemonte , N. ; Galietta , L. J. V. ; Mazzei , M. T. ; Fossa , P. ; Giampieri , M. ; Mazzei , M. Synthesis of 4-thiophen-2′-yl-1,4-dihydropyridines as potentiators of the CFTR chloride channel . Bioorg. Med. Chem. 2009 , 17 , 7894 ; (d) Hilgeroth , A. ; Baumeister , U. ; Heinemann , F. W. Novel solid-state synthesis of polyfunctionalized 3,9-diazatetraasteranes . Eur. J. Org. Chem. 1998 , 1213 .
   PubMed Web of Science ®Google Scholar
• (a) Triggle , D. J. ; Langs , D. D. ; Janis , R. A. Calcium channel ligands: Structure–function relationships of the 1,4-dihydropyridines . Med. Res. Rev. 1989 , 9 , 123 ; (b) Safak , C. ; Simsek , R. Fused 1,4 dihydropyridines as potential calcium modulatory compounds . Mini-Rev. Med. Chem. 2006 , 7 , 747 .
   PubMed Web of Science ®Google Scholar
• Peri , R. ; Padmanabhan , S. ; Rutledge , A. ; Singh , S. ; Triggle , D. J. Permanently charged chiral 1,4-dihydropyridines: Molecular probes of l-type calcium channels: Synthesis and pharmacological characterization of methyl (ω-trimethylalkylammonium)1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylateiodide, calcium channel antagonists . J. Med. Chem. 2000 , 43 , 2906 .
   PubMed Web of Science ®Google Scholar
• Alajarin , R. ; Vaquero , J. J. ; Alvarez-Builla , J. ; Pastor , M. ; Sunkel , C. ; Fau de Casa-Juana , M. ; Priego , J. ; Statkow , P. R. ; Sanz-Aparicio , J. ; Fonseca , I. Synthesis, structure, and pharmacological evaluation of the stereoisomers of furnidipine . J. Med. Chem. 1995 , 38 , 2830 .
   PubMed Web of Science ®Google Scholar
• Klusa , V. Cerebrocrast, neuroprotectant, cognition enhancer . Drugs Future 1995 , 20 , 135 .
   Google Scholar
• Briede , J. ; Daija , D. ; Stivrina , M. ; Duburs , G. Effect of cerebrocraston the lymphocyte blast transformation activity in normal and streptozotocin-induced diabeticsrats . Cell. Biochem. Func. 1999 , 17 , 89 .
   PubMed Web of Science ®Google Scholar
• Hantzsch , A. Ueber die syntheses pyridineartiger verbindungen aus acetessigäther und aldehydammoniak. Justus Liebigs Ann. Chem. 1882, 1, 215.
   Google Scholar
• (a) Huang , Z. ; Hu , Y. ; Zhou , Y. ; Shi , D. Efficient one-pot, three-component synthesis of fused pyridine derivatives in ionic liquid . Comb. Sci. 2011 , 13 , 45 ; (b) Alizadeh , A. ; Firuzyar , T. ; Mikaeili , A. Efficient one-pot synthesis of spirooxindole derivatives containing 1,4-dihydropyridine-fused-1,3-diazaheterocycle fragments via four-component reaction . Synthesis 2010 , 22 , 3913 .
   Google Scholar
• Curini , M. ; Cravotto , G. ; Epifano , F. ; Giannone , G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins . Curr. Med. Chem. 2006 , 13 , 199 .
   PubMed Web of Science ®Google Scholar
• O'Kennedy , P. ; Thornes , R. D. (Eds.); Coumarins: Biology, Applications, and Mode of Action ; Wiley : Chichester , U. K , 1997 .
   Google Scholar
• Abd-Allah , O. A. Synthesis and biological studies of some benzopyrano [2,3-c] pyrazolederivatives . Farmaco 2000 , 55 , 641 .
   PubMedGoogle Scholar
• El-Agrody , A. M. ; El-Latif , M. S. A. ; El-Hady , N. A. ; Fakary , A. H. ; Bedair , A. H. Heteroaromatization with 4-hydroxycoumarin, part II: Synthesis of some new pyrano[2,3-d]pyrimidines, [1,2,4]triazolo[1,5-c]pyrimidines and pyrimido[1,6-b]-[1,2,4]triazinederivatives . Molecules 2001 , 6 , 519 .
   Web of Science ®Google Scholar
• Nofal , Z. M. ; El-Zahar , M. I. ; El-Karim , S. S. A. Novel coumarin derivatives with expected biological activity . Molecules 2000 , 5 , 99 .
   Web of Science ®Google Scholar
• Hepworth , J. D. ; Gabbutt , C. D. ; Heron , B. M. In Comprehensive Heterocyclic Chemistry II ; A. Katritzky , C. W. Rees , E. F. V. Scriven (Eds.); Pergamon Press : Oxford , 1996 ; Vol. 5 , chapter 5.07 , pp. 301 – 350 .
   Google Scholar
• Hepworth , J. D. ; Gabbutt , C. D. ; Heron , B. M. In Comprehensive Heterocyclic Chemistry II ; A. Katritzky , C. W. Rees , and E. F. V. Scriven (Eds.); Pergamon Press : Oxford , 1996 ; Vol. 5 , chapter 5.08 , pp. 351 – 468 .
   Google Scholar
• Burke , T. R. ; Lim , B. ; Marquez , V. E. ; Li , Z. H. ; Bolen , J. B. ; Stefanova , I. ; Horak , I. D. Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck . J. Med. Chem. 1993 , 36 , 425 .
   PubMed Web of Science ®Google Scholar
• Huang , C. K. ; Wu , F. Y. ; Ai , Y. X. Polyhydroxylated 3-(N-phenyl)carbamoyl-2-iminochromene derivatives as potent inhibitors of tyrosine kinase p60(c-src) . Bioorg. Med. Chem. Lett. 1995 , 5 , 2423 .
   Web of Science ®Google Scholar
• Mhiri , C. ; El Gharbi , R. ; Le Bigot , Y. Polymer-supported reagents: Novel methodology for selective and general synthesis of iminocoumarins . Synth. Commun. 1999 , 29 , 3385 .
   Web of Science ®Google Scholar
• Ghahremanzadeh , R. ; Amanpour , T. ; Bazgir , A. Pseudo-four-component synthesis of benzopyranopyrimidines . Tetrahedron Lett. 2010 , 51 , 4202 .
   Web of Science ®Google Scholar
• (a) Alizadeh , A. ; Rezvanian , A. Practical and novel one-pot protocol for the synthesis of highly functionalized pyridinols and pyrido[1,2-a]-fused-1,3-diazaheterocycles . Synlett 2011 , 8 , 1105 ; (b) Alizadeh , A. ; Zarei , A. ; Rezvanian , A. A novel and one-pot multicomponent approach to the synthesis of dihyroindeno[1,2-b]pyrroles and indeno[2,1:4,5]pyrrolo[1,2-a]-fused 1,3-diazaheterocycles . Synthesis 2011 , 3 , 497 ; (c) Alizadeh , A. ; Rezvanian , A. ; Yuan , D. Novel heterocyclic β-nitroenamines-based on a one-pot three-component reaction: A facile synthesis of fully substituted 1H-pyrrolo[1,2-a]-fused-1,3-diazaheterocycles . Tetrahedron 2010 , 66 , 9933 ; (d) Alizadeh , A. ; Ghanbaripour , R. A novel and efficient synthesis of 3-[(4,5-dihydro-1H-pyrrol-3-yl)carbonyl]-2H-chromen-2-ones (=3-[(4,5-dihydro-1H-pyrrol-3-yl)carbonyl]-2H-1-benzopyran-2-ones) . Helv. Chim. Acta 2013 , 96 , 473 – 477 .
   Web of Science ®Google Scholar
• Volmajer , J. ; Toplak , R. ; Leban , I. ; Le Marechal , A. M. Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazonocompounds . Tetrahedron 2005 , 61 , 7012 .
   Web of Science ®Google Scholar