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A METHOD FOR ISOLATION OF AN ORTHO QUINONE METHIDE INTERMEDIATE

[Category : - Organic Chemistry]
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Exemplary embodiments of the present disclosure are directed towards a very first method for
isolation of naphthalene based ortho quinone intermediate, wherein the ortho quinone intermediate
is 2-oxonaphthalen-1(2H)-ylidene) methyl trifluoromethanesulfonate. It is isolated from 2-
hydroxynaphthalene-1-carbaldehyde by adding predetermined amounts of dry dichloromethane, dry
pyridine and triflic anhydride under specific reaction conditions. The isolation of ortho quinone
intermediates would pave way for generation of derivatives of 2-hydroxynaphthalene-1-
carbaldehyde with substitution at positions other than the 6th position, with applications in medicine
and other fields.

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Several commercial drug molecules such as Sirtinol, Splitomicin, Cambinol etc. have 2-
hydroxynaphthalene-1-carbaldehyde derivatives as their active moiety. There exists several natural
products with 2-hydroxynaphthalene-1-carbaldehyde skeleton such as Gossypol, Hemigossypol,
Methoxyhemigossypol, Stelladerol etc. Synthetic derivatives of 2-hydroxynaphthalene-1-
carbaldehyde with substitutions at 6th position are extensively studied but there is a dearth of
research on derivatives with substitutions at other positions. Generation of such derivatives will
open new avenues for their applications in medicinal chemistry, material science, sensors, probes in
medical imaging, radioactive imaging tags etc.

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