A Facile Route to Phenylselanyl Substituted Pyrano[3,2-c]chromenes
Kois, Pavol; Metwally El-Shaaer, Hafez; Lacova, Margita;
Abstract
The synthesis of a new family of phenylselanyl substituted pyrano[3,2-c]
chromenes is presented. The cyclocondensation reaction of 3-formylchromones 1 with
phenylselanylacetic acid 2 in acetic anhydride under mild conditions gave the novel 3-
(phenylselanyl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetates P1 in 80% yield.
Further treatment of acetates P1 with ethanolic or aqueous medium led to the
corresponding 5-ethyloxy-3-(phenylselanyl)-2-oxo-2H,5H-pyrano[3,2-c]chromen P3 and
3-(phenylselanyl)-2H,5H-pyrano[3,2-c]chromen-5-ol P4 , respectively. We found the
reaction of phenylselanylacetic acid with arylcarbaldehydes in acetanhydride at room
temperature yielded the corresponding 2-(phenylselanyl)cinnamoyl acid P5. This reaction
at elevated temperature, under reflux or in the solventless mixture at 180o
C led only to
the diphenyl-diselane P6 and a pitch polymer
chromenes is presented. The cyclocondensation reaction of 3-formylchromones 1 with
phenylselanylacetic acid 2 in acetic anhydride under mild conditions gave the novel 3-
(phenylselanyl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetates P1 in 80% yield.
Further treatment of acetates P1 with ethanolic or aqueous medium led to the
corresponding 5-ethyloxy-3-(phenylselanyl)-2-oxo-2H,5H-pyrano[3,2-c]chromen P3 and
3-(phenylselanyl)-2H,5H-pyrano[3,2-c]chromen-5-ol P4 , respectively. We found the
reaction of phenylselanylacetic acid with arylcarbaldehydes in acetanhydride at room
temperature yielded the corresponding 2-(phenylselanyl)cinnamoyl acid P5. This reaction
at elevated temperature, under reflux or in the solventless mixture at 180o
C led only to
the diphenyl-diselane P6 and a pitch polymer
Other data
Title | A Facile Route to Phenylselanyl Substituted Pyrano[3,2-c]chromenes | Authors | Kois, Pavol; Metwally El-Shaaer, Hafez ; Lacova, Margita | Keywords | 2-Oxopyrones;Cyclization reactions;Nucleophilic;Benzopyranes;Aldol | Issue Date | 2005 | Journal | 9th International Elctronic Conference on Synthesis Organic Chemistry, ECSOC-9 1-30 Nov. 2005 | DOI | 10.3390/ecsoc-9-01520 |
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