A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes
Lacova, M; Gasparova, R; Kois, P; Bohac, A; Metwally El-Shaaer, Hafez;
Abstract
The synthesis of phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes 4 is accomplished via cyclocondensation of 4-oxo-4H-chromen-3-carbaldehydes 1 with appropriately substituted acetic acids 2 under mild conditions. Further treatment of 4 with alcohol or water led to 5-alkoxy- and 5-hydroxy-2H,5H-pyrano[3,2-c]chromen-2-ones 5 and 6, respectively. Acid and thermal catalysed rearrangement of 4-6 gave 5-hydroxypyrano[2,3-b]chromen-2(10aH)-ones 7 and their subsequent substitution led to 5-alkoxyderivatives 8. Reaction of 4 with amides led to 5-acylamino or 5-phenylsulfonamino substituted 2H,5H-pyrano[3,2-c]chromen-2-ones 9. Reactions were performed under heating or microwave irradiation. © 2009.
Other data
Title | A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes | Authors | Lacova, M; Gasparova, R; Kois, P; Bohac, A; Metwally El-Shaaer, Hafez | Keywords | DERIVATIVES;Chromenes;Antineoplastic activity;Microwave;Acetic acids;Rearrangement;Condensation;CHIRAL SELENIUM-COMPOUNDS;ORGANIC-SYNTHESIS;CHEMICAL-SHIFTS;ACIDS;CONDENSATION;COUMARIN;CHEMISTRY;3-FORMYLCHROMONES;CHROMONES | Issue Date | 2010 | Publisher | PERGAMON-ELSEVIER SCIENCE LTD | Journal | Tetrahedron | ISSN | 0040-4020 | DOI | 10.1016/j.tet.2009.11.057 | Scopus ID | 2-s2.0-73649134691 | Web of science ID | WOS:000274591900036 |
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