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Synthese und Eigenschaften von Thiazolo[3,2‐ a ]pyrimidinen und Thiazolo [3,2‐ a ] pyrrolo [2,3‐ d ]pyrimidinen
Author(s) -
Bormann G.,
Troxler F.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540620
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , bromine , acetal , derivative (finance) , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
From the alkali‐catalysed reaction of thiouracil with bromoacetaldehyde diethyl acetal three products are isolated in nearly the same quantity: 2‐(2, 2‐diethoxyethylthio)‐uracil ( 2 ) and two cyclization products: 3 , a thiazolo[3, 2‐ a ]pyrimidin‐5‐one, and 4 , athiazolo[3, 2‐ a ]pyrimidin7‐one. By warming with acid both 2 and 4 yield 3 . Rearrangement of 4 to 3 proceeds also by heating the hydrochloride. Similar cyclizations leading to thiazolo[3, 2‐ d ]pyrrolo[2, 3‐d]pyrimidin‐5‐ones are also described. Bromine substitutes 3 in position 6. The bromo derivative 6 on treatment with primary or secondary amines affords 7‐amino compounds.