STUDIES IN THE CYCLOPROPANE SERIES.[THIRD PAPER.]

STUDIES IN THE CYCLOPROPANE SERIES.

111.

240.5

nucleoside (I) into dimethylglyoxalone (XXXVIII) therefore may be represented as follows : NH - CO

I CO 1

NH?

I I --t CO CH II PH3 I

COOH

NH-C

I CH --f Lo / I PH3 I

NH - C.CHOH (1). (XXXV). I NH - C : CHCOOH NH - C.CH8

NH

I I

- C.CH.OH

J

I

A0

I

1

NHz

/OH CH.CH8

.1

1 (xxxvl). - C : CHI

NH

A0

t-

I

NH - C.CH3 (XXXVIII).

NH - CHCHs (XXXVII).

1

= CHz

1

NH - CHCHD (XXXIX).

Our resuIts show conclusively that a simple primary or secondary alcoholic grouping in position 4 of the uracil molecule cannot be removed from the pyrimidine by hydrolysis with acids with production of uracil. Whether a lengthening of the carbon chain and the introduction of other hydroxyl groups into such a grouping will weaken the attraction between the carbon atom 4 and the side chain remains to be established. An investigation planned to develop a method of synthesizing tertiary pyrimidine-nucleosides (XI,) is now in progress. It will be of interest to determine whether such combinations will undergo rearrangements by hydrolysis giving combinations corresponding to Formula XLI. NH - CO

I

CO

I

NH

NH-C:

1 CH I / /OH

HzO

+

CHz

i l

coz + CO

- C.C-R

AH - C