Thioimideazoles useful as intermediates for preparing thiazine

Details Thioimideazoles useful as intermediates for preparing thiazine Thioimideazoles useful as intermediates for preparing thiazine

1991-09-26

1992-11-17

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D23384

Patent

active

051645114

ABSTRACT:
Novel thioimidazoles are 5-carboxyaldehyde-1-methyl-4-(phenylmethyl)thioimidazole and 5-(.alpha.-aminoacetyl)-1-methyl-4-(phenylmethyl)thioimidazole acid addition salt. The latter is prepared from the former by steps comprising Grignard addition to form 5-(1-hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole, oxidizing the hydroxy compound to form the corresponding ketone, brominating under acidic conditions to form the bromoacetyl derivative, converting the bromo in the bromoacetyl derivative to N,N-diformylamino and then hydrolyzing. The latter thioimidazole is an intermediate for forming 5-methylimidazo[4,5-e]-1,2-thiazin-4(5H)-one, that is neamphine, and for forming 3-chloro-(5-methylimidazo) [4,5-e]-1,2-thiazin-4(5H)-one, that is 3-chloroneamphine.

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