Convenient Synthesis of Heterocyclic Compounds with Dihydropyrano[3,4-b]pyridine Scaffold

REFERENCES

• da-Cunha , E. V. L. ; Cornelio , M. L. ; Barbosa-Filho , J. M. ; Braz-Filho , R. ; Gray , A. I. Eletefine, a stephaoxocane alkaloid from Cissampelos glaberrima . J. Nat. Prod. 1998 , 61 ( 9 ), 1140 – 1142 .
   PubMed Web of Science ®Google Scholar
• Cueva , J. P. ; Giorgioni , G. ; Grubbs , R. A. ; Chemel , B. R. ; Watts , V. J. ; Nichols , D. E. trans-2,3-Dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: Synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D-1 receptor full agonist . J. Med. Chem. 2006 , 49 ( 23 ), 6848 – 6857 .
   PubMed Web of Science ®Google Scholar
• Przybyla , J. A. ; Cueva , J. P. ; Chemel , B. R. ; Hsu , K. J. ; Riese , D. J. ; McCorvy , J. D. ; Chester , J. A. ; Nichols , D. E. ; Watts , V. J. Comparison of the enantiomers of (±)-doxanthrine, a high efficacy full dopamine D-1 receptor agonist, and a reversal of enantioselectivity at D-1 versus alpha(2C) adrenergic receptors. Eur. Neuropsychopharmacol. 2009, 19(2), 138–146.
   PubMed Web of Science ®Google Scholar
• Millan , M. J. ; Seguin , L. ; Gobert , A. ; Cussac , D. ; Brocco , M. The role of dopamine D-3 compared with D-2 receptors in the control of locomotor activity: A combined behavioural and neurochemical analysis with novel, selective antagonists in rats . Psychopharmacology 2004 , 174 ( 3 ), 341 – 357 .
   PubMed Web of Science ®Google Scholar
• Eiden , F. ; Wanner , K. T. 5,6-Dihydro-2H-pyran-3(4H)-one as a synthon for pyran-annulated heterocyclic compounds . Liebigs Ann. Chem. 1984 , 11 , 1759 – 1777 .
   Google Scholar
• Biedrzycki , M. ; De Bie , D. A. ; Van Der Plas , H. C. Intramolecular inverse-electron demand Diels-Alder reaction of pyrazines . Tetrahedron 1989 , 45 ( 19 ), 6211 – 6220 .
   Web of Science ®Google Scholar
• Sall , C. ; Desbois , N. ; Paquelet , S. ; Camacho , J. R. ; Chezal , J. M. ; Teulade , J. C. ; Blache , Y. An efficient route to a 5,6-dihydropyrano[3,4-b]pyridin-8-one core in two steps from enaminolactones . Tetrahedron Lett. 2008 , 49 ( 8 ), 1301 – 1304 .
   Web of Science ®Google Scholar
• Wall , M. E. ; Wani , M. C. ; Cook , C. E. ; Palmer , K. E. ; Mc Phail , A. T. ; Sim , G. A. Plant antitumor agents, I: Isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata . J. Am. Chem. Soc. 1966 , 88 ( 16 ), 3888 – 3890 .
   Web of Science ®Google Scholar
• Grassy , G. ; Teulade , J. C. ; Chapat , J. P. ; Simeon De Buochberg , M. ; Atisso , M. Utilization of Q.S.A.R multidimensional analysis methods, I: Application to multiple biological responses . Eur. J. Med. Chem. 1982 , 17 ( 2 ), 109 – 115 .
   Web of Science ®Google Scholar
• Grierson , D. The Polonovski reaction . Org. React. 1990 , 39 , 85 – 295 .
   Google Scholar
• Toche , R. B. ; Ghotekar , B. K. ; Kendre , D. B. ; Kazi , M. A. ; Jachak , M. N. An efficient synthesis of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines from 5-aminopyrazoles and cyclic beta-keto ester . J. Heterocycl. Chem. 2008 , 45 ( 6 ), 1711 – 1717 .
   Web of Science ®Google Scholar
• Hefner , J. ; Langer , P. Chelation control in the [3 + 3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes . Tetrahedron Lett. 2008 , 49 ( 29–30 ), 4470 – 4472 .
   Google Scholar
• Garcia , D. ; Foubelo , F. ; Yus , M. Regioselective reductive opening of substituted phthalans: Synthetic applications . Tetrahedron 2008 , 64 ( 19 ), 4275 – 4286 .
   Google Scholar