Abstract
AbstractAlkyl (1‐cyclohexen‐1‐yl)carbamoyl chlorides (1) react with thiocyanate ion to form enecarbamoyl thiocyanates (2). In pyridine solution 2 readily isomerizes to the isothiocyanate 4, which however is not isolated, but immediately transformed in good yields to tetrahydro‐4‐thio‐2,4(lH,3H)quinazolinediones (3). Various transformations of 3, including conversion to tetra‐hydro‐2,4(2H,4H)quinazolinedione (5), dithione (6), alkylation products (8 and 9), sodium salts 11 and Raney nickel degradation to 4,4a,5,6,7,8,8a‐octahydro‐l‐methyl‐2(1H)quinazolinone (7), were carried out to investigate their chemistry and substantiate structural assignments.
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