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Synthesis and Photoreaction of a‐Methylene‐γ‐Butyrolactone‐Psoralen Heterodimers
Author(s) -
GiménezArnau Elena,
Bussey Cécile,
Lepoittevin JeanPierre
Publication year - 1997
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1997.tb08564.x
Subject(s) - psoralen , intramolecular force , chemistry , pyrone , methylene , yield (engineering) , double bond , molecule , derivative (finance) , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , materials science , dna , biochemistry , economics , financial economics , metallurgy
Three double‐headed molecules were synthesized by linking a photoreactive linear (1, 2) or angular (3) furocou‐marin via a linear 10‐ or 5‐carbon chain to an electro‐philic α‐methylene‐γ‐butyrolactone. The photochemical behavior of these molecules was investigated in ethanol at 365 nm and the photocycloadducts obtained from each compound were isolated and characterized. In all cases, the photoreactivity results showed the 3,4‐pyrone double bond of the psoralen (linear or angular) to be the most reactive and [2 + 2] intramolecular photocycloadducts between the 3,4‐pyrone and the exomethylenic double bonds were obtained. With compounds 1 and 2, two kinds of intramolecular photocycloadducts were obtained, namely cissyn‐exo derivatives in 46% and 36% yield, respectively, and trans‐syn‐exo derivatives in 14% and 18% yield, respectively. With compound 3, only the trans‐syn‐exo derivative was obtained in 33% yield.