|dc.description.abstract||The work in this thesis mainly deals with l,l-enediamines and ~ -substituted
enamines (push-pull olefines) and their reactions, leading to the formation of a number of
Various ~-substituted enamines were prepared by a 'one pot synthesis' in which a
l,l-enediamine presumably acts as an intermediate. These enamines, various substituted
crotonamides and propenamides, were made by using two different orthoesters, various
secondary and primary amines and cyanoacetamide. Their structures, mechanism of
formation and geometry are discussed.
A synthetic route to various unsymmetrically substituted pyridines was examined.
Two substituted pyridinones were obtained by using two different ~-substituted enamines
and cyanoacetamide. In one case a dihydropyridine was isolated. This dihydropyridine, on
heating in acidic conditions, gave a pyridinone, which confirmed this dihydropyridine as
an intermediate in this pyridine synthesis.
A new synthetic method was used to make highly substituted pyridinones, which
involved the reaction of l,l-enediamines with the ~-substituted enamines. A one pot
synthesis and an interrupted one pot synthesis were used to make these pyridinones. Two
different orthoesters and three different secondary amines were used. Serendipitous
formation of a pyrimidinone was observed when pyrrolidine was used as the secondary
amine and triethyl orthopropionate was used as the orthoester. In all cases cyanoacetamide
was used as the carbon acid. This pyridine synthesis was designed with aI, l-enediamine
as the Michael donor and the ~ -substituted enamines as Michael acceptors.
Substituted ureas were obtained in two cases, which was a surprise.
Some pyrimidines were made by reacting two substituted enamines with two
different amidines. When benzamidine was used, the expected pyrimidines were obtained.
But, when 2-benzyl-2-thiopseudourea (which is also an amidine) was used, of the two
expected pyrimidines, only one was obtained. In the other case, an additional substitution
reaction took place in which the S-benzyl group was lost.
An approach to quinazolone and benzothiadiazine synthesis is discussed. Two
compounds were made from 1, I-dimorpholinoethene||en_US