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Synthesis and Photooxygenation of Linear and Angular Furocoumarin Derivatives as a Hydroxyl Radical Source: Psoralen, Pseudopsoralen, Isopseudopsoralen, and Allopsoralen
Author(s) -
Elgogary Sameh Ramadan,
Hashem Neveen Mohamed,
Khodeir Mohamed Nabeel
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2084
Subject(s) - photooxygenation , furocoumarins , furocoumarin , chemistry , psoralen , cycloaddition , singlet oxygen , photochemistry , dichlorocarbene , chloroform , organic chemistry , oxygen , catalysis , dna , biochemistry
Synthesis of linear and angular furocoumarins with new skeleton structure of potential photobiological feature interest was carried out through Williamson reaction of hydroxycoumarins with 3‐chloro‐2‐butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer ( 1 O 2 ). The photooxygenation reactions afforded the photocleaved product through [2 + 2] cycloaddition and the photooxygenated products through ene reaction and [4 + 2] cycloaddition . The photoproducts were isolated and fully characterized by spectral analyses.