Synthesis and Heterocyclization of4-(Alkenylsulfanyl)quinazolines
2020
Alkylation of quinazoline-4(3H)-thione with
3-chloro-2-methylpropene and 2,3-dibromopropene afforded previously unknown
4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline and
4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline, respectively.
4-[(Prop-2-en-1-yl)sulfanyl]quinazoline reacted with bromine to give
bromocyclization product and product of bromine addition to the exocyclic double
bond. The reaction of 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline with
halogens involved thiazole ring fusion.
5-Bromo-3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium bromide was isolated in the reaction of
4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline with bromine, and the reaction of
the same substrate with iodine gave a mixture of
3-bromo-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium and
3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium iodides.
4-[(2-Methylprop-2-en-1-yl)sulfanyl]quinazoline reacted with 2 equiv of iodine
to produce 3-methyl-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium triiodide and pentaiodide; the
structure of the latter was studied by X-ray diffraction.
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