Several 2-pyridylmethylene-1-indanones (I) were prepared and reduced to Z-pyridylmethyl-1-indanones (11). The reductive cyclization of 5,6-dimethoxy-and 6-hydroxy-5methoxy-2-pyridylmethylene-1-indanone gave the corresponding 5a, 6,6a, 7,8,9,10, llaoctahydroindeno[Z, 1-blindolizines ( X ) . W e reported earlier (2,3) the Knoevanagel reaction of 1-indanone with 2-and 3-pyridinecarboxaldehyde and the reduction of the resultant products to the corresponding 2pyridylmethylene-1-indanones. Jn a continuation of this work, several substituted 1indanones were prepared and condensed with 2-, 3-, and 4 -pyridinecarboxaldehyde in the presence of piperidine acetate a s catalyst. In general, a higher temperature and longer reaction time than those employed with 1-indanone were required. Table I summarizes the data on the Z-pyridylmethylene-lindanones (I) that were prepared.Anal. Calcd. f o r C t , H 2 a C l N~: C , 65.3; H, 7.9; N , 4.3. Found: C, 65.2; H ,7 . 7 ; N, 4.4. Method B.
5-Methoxy-1-0x0-6-indanyl isobutyrate. Method A.A stirred suspension of 6.0 g. (0.021 mole) of 5,6-dimethoxy-2-Received S e p t e m b c r 13, 1965 University, Mississippi
The Beckmann rearrangement of 5-methylthiaindan-4-one oximes (I) and thiaindan-6one oximes (IV) proceeds with the migration of the alkyl group to yield dihydrothienopyridones (I1 and V, respectively). In two instances, the corresponding lactones (VIIa
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