196

UNDERGRADUATE ORGANIC CHEMISTAy

Condensation of urea with substituted
malonic esters
compounds called barbiturates. produces a clae.
Barbiturates
character. They from salts with acids. Free
are
cyclic diimides and are acidie
barbiturates and their salts
sedatives, soporifics and anesthetics. are
The familiar drugs barbitones,
barbiturates and may be
phenobarbital and
pentobarbital (Nembutal)
synthesised as below are

i) C2H5O
CHs COOEt
CzHOH CHs C-NH
coOEN-C--NH,-

CH (i) H2O
C2H NH 0

Barbitone

i) CaHO/
CgHs COOEt
NH2 C=0
NH2 C2H5OH CHs C-NH
C2Hs COOEt NH2 i) H2o H -NH
C=0
Diethyl ethyl phenyl
malonate O
Phenobarbital
CH3
(CH2)2
CH3-CHH COOEt

CaHs cOOEt NH2c0

NH2
Diethyl ethyl (1-methylbutyl)
malonate
6) CzH,oCH,OH
i) H2O

CH3
(CHa)
CH-CH. C-NH
NHCo

CaHs C-NH
O
Nembutal

5.4 DITHIANES

The sulphur atom of thiol is far better nucleophile than the oxygen atom of an
alcohol. Thiols add to the carbonyl group of aldehydes and ketones to form
tetrahedral carbonyl addition compounds. A common and most useful sulphur
nucleophile used for this purpose is 1, 3-propanedithiol. The carbonyl group of both
aldehydes and ketones react with this compound in the presence of an acid catalyst
to form cyclic thio acetals which is called 1, 3-dithianes.