143882-71-7Relevant academic research and scientific papers
Furocoumarins: Part 34 - Synthesis and stereochemistry of dihydrofurocoumarins
Rao, S S Madhava,Trivedi, K N
, p. 488 - 491 (2007/10/02)
7-Cinnamyloxy-4-methylcoumarin (1a) on Claisen rearrangement in N,N-dimethylaniline furnishes a cyclised angular dihydrofurocoumarin (4) and two open chain products (2 and 3a). 2 and 3a on cyclisation with conc.H2SO4 yield the corresponding dihydrofurocoumarins (8a and 11).Stereochemistry of dihydrofurocoumarins 4 and 8a has been studied using NOE difference spectra.Catalytic hydrogenation of 3,7-dimethyl-2-phenylfurobenzopyran-5(H)-one (6) and 2,7-dimethyl-3-phenylfurobenzopyran-5(H)-one (9a) furnish the corresponding cis isomers 7 and 10.Similarly,the stereochemistry of other dihydrofurocoumarins (12 and 3b) obtained by cyclisation of open chain products from Claisen rearrangement of 7-cinnamyloxy-8-iodo-coumarin were also studied.Furocoumarins 9b and 14 were also synthesised.
