Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 10
258
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

A Convenient Approach to the Synthesis of Dialkyl 5‐Oxo‐1,2‐dihydro‐5H‐chromeno [4,3‐b]pyridine‐2,3‐dicarboxylates

&
Pages 1579-1588 | Received 25 Oct 2007, Published online: 24 Apr 2008

References

  • Ukawa , K. , Ishiguro , T. , Wada , Y. and Nohara , A. 1986 . Synthesis of 5‐oxo‐5H‐[1]benzopyrano[4,3‐b]pyridine derivatives . Heterocycles , 24 : 1931 – 1941 .
  • Sun , W. , Cama , L. D. , Birzin , E. T. , Warrier , S. , Locco , L. , Mosley , R. , Hammond , M. L. and Rohrer , S. P. 2006 . 6H‐Benzo[c]chromene‐6‐one derivatives as selective ERβ agonists . Bioorg. Med. Chem. Lett. , 16 : 1468 – 1472 .
  • Pave , G. , Charald , P. , Viauld‐Massuard , M.‐C. , Troin , Y. and Guillaumet , G. 2003 . New efficient synthesis of pyrido[2,3‐c] and pyrido[3,2‐c]coumarin derivatives . Synlett , : 987 – 990 .
  • Lewis , W. H. , Stonard , R. J. , Porras‐Reyes , A. T. , Mustoe , T. A. and Thoms , A. Wound‐healing composition . US Patent 5156847 . 1992 . Chem. Abstr. 1992, 117, 245630t
  • Connor , D. T. , Unangst , P. C. , Schwender , C. F. , Sorensen , R. J. , Carethers , M. E. , Puchalski , C. , Brown , R. E. and Finkel , M. P. 1989 . 3‐(Aminoalkyl)‐1,2,3,4‐tetrahydro‐5H‐[1]benzopyrano[3,4‐c] pyridine‐5‐ones as potential anticholinergic bronchodilators . J. Med. Chem. , 32 : 683 – 688 .
  • Heber , D. 1978 . 5H‐[1]benzopyrano[4,3‐b]pyridine by condensation of 3‐acylchromones with enamines . Synthesis , : 691 – 692 .
  • Heber , D. 1983 . Reactions of heterocycles containing the 2‐acyl‐2‐propenone structure, II: Pyrido[2,3‐d]pyrimidines from 4‐oxo‐4H‐chromene‐3‐carbaldehydes and 4‐aminouracils . Arch. Pharm. , 316 : 55 – 62 .
  • Heber , D. 1987 . Reactions of heterocycles containing the 2‐acyl‐2‐propenone structure, III: Pyrido[3,2‐c]‐coumarins from 3‐substituted 1‐benzopyrans and enamines . Arch. Pharm. , 320 : 402 – 406 .
  • Heber , D. 1987 . Reactions of heterocycles containing the 2‐acyl‐2‐propenone structure, V: [1]Benzopyrano[4,3‐b]pyridine‐2,5‐(2H,5H)‐diones by cyclisation of 3‐substituted 4‐aminocoumarins . Arch. Pharm. , 320 : 577 – 581 .
  • Heber , D. 1987 . Reactions of heterocycles containing the 2‐acyl‐2‐propenone structure, VI: Novel preparation of 6‐oxo‐6H‐[1]benzopyrano[4,3‐b]quinoline derivatives . Arch. Pharm. , 320 : 595 – 599 .
  • Heber , D. and Berghaus , T. 1994 . Synthesis of 5H‐[1]benzopyrano[4,3‐b]pyridine‐5‐ones containing an azacannabinoidal structure . J. Het. Chem. , 31 : 1353 – 1359 .
  • Winn , M. , Arendsen , D. , Dodge , P. , Dren , A. , Dunningan , D. , Hallas , R. , Hwang , K. , Kyncl , J. , Lee , Y.‐H. , Plotnikoff , N. , Young , P. and Zaugg , H. 1976 . Drugs derived from cannabinoids, 5: Δ6a,10a‐Tetrahydrocannabinol and heterocyclic analogs containing side chains . J. Med. Chem. , 19 : 461 – 471 .
  • Wolfbeis , O. S. 1978 . Luminescent heterocycles, part 8: Synthesis and properties of new hydoxy‐substituted coumarin‐derived laser dyes . Monats. Chem. , 109 : 1413 – 1421 .
  • Razdan , R. J. 1981 . “ The total synthesis of cannabinoids ” . In The Total Synthesis of Natural Products Edited by: ApSimon , J. Vol. 4 , 186 – 262 . New York : John Wiley and Sons .
  • Majumdar , K. C. and Bhattacharyya , T. 2001 . Synthesis of bioactive heterocycles: Amino Claisen rearrangement of 4‐N‐(4‐aryloxybut‐2ynyl)‐N‐methylaminocoumarins . Tetrahedron Lett. , 42 : 4231 – 4233 .
  • Chatterjea , J. N. , Shaw , S. C. , Singh , J. N. and Singh , S. N. 1977 . Synthesis of condensed pyridines, part I: Pyrido[3,2‐c]coumarins . Ind. J. Chem. Sec. B , 15 : 430 – 431 .
  • Darbarwar , M. and Sundaramurthy , V. 1982 . Synthesis of coumarines with 3∶4‐fused ring systems and their physiological activity . Synthesis , : 337 – 388 . and references therein
  • O'Callaghan , C. N. 1987 . Synthesis of dialkyl 2‐(2‐hydroxyphenyl)‐4,6‐dimethyl‐1,2‐dihydropyridine‐3,5‐dicrboxylates and alkyl 2,4‐dimethyl‐5‐oxo‐5H‐[1]benzopyrano[4,3‐b]pyridine‐3‐carboxylates . Synthesis , : 499 – 503 .
  • Heber , D. , Ivanov , I. C. and Karagiosov , S. K. 1995 . The Vilsmeier reaction in the synthesis of 3‐substituted [1]benzopyrano[4,3‐b]pyridine‐5‐ones . J. Het. Chem. , : 505 – 509 .
  • Ghosh , C. K. , Ray , A. and Patra , A. 2001 . Benzopyrans, part 42[1]: Reactions of 4‐oxo‐4H‐1‐benzopyran‐3‐carbaldehyde with some active methylene compounds in the presence of ammonia . J. Het. Chem. , : 1459 – 1463 .
  • Murphy , P. J. and Brennan , J. 1988 . The Wittig olefination reaction with carbonyl compounds other than aldehydes and ketones . Chem. Soc. Rew. , 17 : 1 – 30 .
  • Pars , H. G. , Granchelli , F. E. , Razdan , R. K. and Keller , J. K. 1976 . Drugs derived from cannabinoids, 1: Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles . J. Med Chem. , 19 : 445 – 454 .
  • Pars , H. G. , Granchelli , F. E. , Keller , J. K. and Razdan , R. K. 1966 . Physiologically active nitrogen analogs of tetrahydrocannabinols: Tetrahydrobenzopyrano[3,4‐d]pyridines . J. Am. Chem. Soc. , 88 : 3664 – 3665 .
  • Palacios , F. , Alonso , C. , Amezua , P. and Rubiales , G. 2002 . Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine and indole via intramolecular Diels–Alder cycloadditions of neutral 2‐azadienes . J. Org. Chem. , 67 : 1941 – 1946 .
  • Pandya , S. U. , Pandya , U. R. , Hirani , B. R. and Brahmbhatt , D. I. 2006 . One pot synthesis of diarylpyrido[3,2‐c]coumarins . J. Heterocycl. Chem. , 43 : 795 – 798 .
  • Becalli , E. M. , Contini , A. C. and Trimarco , P. 2004 . New synthetic approach to [1]benzopyrano[4,3‐b]pyridin‐5‐one derivatives . Tetrahedron Lett. , 45 : 3447 – 3449 .
  • Becalli , E. M. , Contini , A. C. and Trimarco , P. 2005 . Substituted coumarin amidines: Useful building blocks for the preparation of [1]benzopyrano[4,3‐b]pyridine‐5‐one and [1]benzopyrano[4,3‐d]pyrimidine‐5‐one derivatives . Tetrahedron , 61 : 4957 – 4964 .
  • Ivanov , I. C. , Karagiozov , S. K. and Manolov , I. 1991 . Synthesis of 4‐(monoalkylamino)coumarins . Arch. Pharm. , 324 : 61 – 62 .
  • Ivanov , I. C. , Karagiozov , S. K. and Simeonov , M. F. 1992 . A facile synthesis of [1]benzopyrano[4,3‐b]pyridine‐5‐ones . Liebigs Ann. Chem. , : 203 – 207 . For additional information on Vilsmeier–Haak formylation of 4‐aminocoumarins, see also Ref. 2d
  • Ivanov , I. C. , Glasnov , T. N. and Heber , D. 2005 . Synthesis of 2H‐chromeno[4,3‐b]pyridine‐2,5(1H)‐diones and related heterocycles via the Erlenmeyer–Ploechl reaction . J. Heterocycl. Chem. , 42 : 857 – 861 .
  • Rad‐Moghadam , K. and Mohseni , M. 2004 . A route to the synthesis of novel coumarins . Monats. Chem. , 135 : 817 – 821 .
  • Adib , M. and Sayahi , M. H. 2006 . An efficient one‐pot synthesis of 4H‐pyrrolo[3,2,1‐ij]quinolines . Monatsh. Chem. , 137 : 207 – 211 .
  • Yavari , I. , Adib , M. and Hojabri , L. 2001 . Vinyltriphenylphosphonium salt mediated synthesis of functionalized coumarines . Tetrahedron , 57 : 7537 – 7540 .
  • Heys , L. , Murphy , P. J. , Coles , S. J. , Gelbirch , T. and Hursthouse , M. B. 1999 . Intramolecular Wittig reactions with lactones utilizing triphenylphosphine and dimethyl acetylenedicarboxylate . Tetrahedron , 40 : 7151 – 7152 .
  • Azizian , J. , Karimi , A. R. , Arefrad , H. , Mohammadi , A. A. and Mohammadizadeh , M. R. 2004 . Synthesis of some novel γ‐spirolactones . Monatsch. Chem. , 135 : 729 – 733 .
  • Yavari , I. and Samzadeh‐Kermani , A. R. 1998 . Vinylphosphonium salt mediated steroselective synthesis of cyclobutene derivatives. A facile route to highly electron‐deficient 1,3‐dienes . 39 : 6343 – 6344 .
  • Evans , L. A. , Griffiths , K. E. , Guthmann , H. and Muphy , P. J. 2002 . Intramolecular Wittig reactions with esters utilizing triphenylphosphine and dimethyl acetylenedicarboxylate . Tetrahedron Lett. , 43 : 299 – 301 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.