الفهرس 
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Abstract
}In !Efficient Syntliesis of nmJef IieterocycEic compoundS via Cf-comp£ex..ation and
conventiona{ metliods .
Summary This thesis aims to synthesize novel heterocyclic compounds via both charge transfer
complexes and conventional methods. Thus it is divided into two main parts:
It deals with synthesis of novel heterocycles via electron donor-acceptor interaction (EDA) between electron rich compounds such as (Z)-2-amino-N-arylbenzimidamide derivatives (51a-k) and (Z)-2-cyano-3-mercapto-3-(phenylamino )-acrylamide (292) with other compounds those are electron poor such as: 7,7,8,8-tetracyanoquinodimethane (TCNQ, 296), 2-dicyanomethylene-indan-l,3-dione (CNIND, 298), tetracyanoethylene (TCNE, 106), 1,4-naphthoquinone (NQ, 305), 2,3-dicyano-l,4-naphthoquinone (DCNQ, 307), 2,31,4-naphthoquinone (DCHNQ, 118) and 2,3-dicyano-5,6-dichloro-l A-benzoquinone (DDQ, 309).
Part II
While the second part is focused on the study of the reactions of some aromatic monooand dialdehydes such as o-phthalaldehyde (314), terephthalaldehyde (293), and 4paracyclophane (108) with (Z)-2-amino-N-arylbenzimidamides (51a,b), (Z)mercapto- 3-(phenylamino )acrylamide (292), 2-amino-4,5 ,6,7 -tetrahydrobenzo[ b ]3-carboxamide (320), and 4-amino-5-substituted-2-(phenylamino )thiophene-3-earboxamide (325a,b).
It deals with studying the interactions between electron rich compounds as (Z)amino-N-arylbenzimidamides (51a-g) with x-deficient compounds as 7,7,8,8quinodimethane (TCNQ, 296) as well as 2-dicyanomethylene-indan-l ,3-dione (CNIND, 298).
Firstly, we have found that on treatment of 2-amino-N-arylbenzimidamides (51 a-g) with 7,7,8,8-tetracyanoquinodimethane (296) in dry ethyl acetate at room temperature, a red CT -complex has been formed followed by the fonnation of a red precipitate. The reaction was followed by TLC. After the end of the reaction (4-7 h) the precipitate was collected by filtration, washed and recrystallized from mixture of DMF/EtOH. The data of the resulting
)!.n CEfficient Syntfiesis of newer fieterocycfic compoutufs via CI-compf.4.ation ana conventiona{ metfwas
Summary
2. Reaction of (Z)-2-cyallo-3-mercapto-3-(phenyLamino)acryLamide (292) with 1,4-
naphthoquinone (NQ, 305)
But in the case of treatment (Z)-2-cyano-3-mercapto-3-(phenylamino )acrylamide (292) with a solution of 1,4-naphthoquinone (305) in dry ethyl acetate (l0 ml), the colour of the solution changed to red. The reaction mixture was stirred at room temperature for 1-3 h, a precipitate started to be formed. After completion of the reaction, the formed precipitate was collected by filtration, washed and recrystallized from DMF/EtOH to afford the product. The spectral data of the product revealed it as 2,7b ][1 ,4]thiazepine-3-carbonitrile (306), (Scheme 99).
’.J
lCN 0 0 6t:t’Ph
Ne{ ~
I NH2 ethyl acetate
a ~ ~ ~ \
HN SH + room temp. _ N CN
I
Ph 0 0
292 305 306
Scheme 99
3. Reactions of (Z)-2-cyano-3-mercapto-3-(phenyLamino)acryLamide (292) with both 2.33dicyano-1,4-naphtlwquillone (DCNQ, 307) and 2.3-dicltloro-1,4-naphtlroquinone (DCHNQ, 118):
We have found that the reaction of (Z)acrylamide (292) with 2.3-dicyano-1,4-naphthoquinone (DCNQ, 307) at room temperature in ethyl acetate occurred via CT-complexation to yield 4,6,11tetrahydronaphtho[2,3-b][ I ,4]thiazepine-3-carbonitrile (308), (Scheme 100).