Synthesis of Novel N, S-Heterocyclic Compounds via Metallacycles
Eman Hassan Khalil Hassan;
Abstract
The subject of this work is the preparation and characterization of some novel organic compounds and organopalladium complexes. This thesis includes the preparation of new heterocyclic systems from 5- methylisatin and Spiro -Palladium complexes using Pd(dba)2 catalyst and various ligands by oxidative addition reaction.
Chapter One "Introduction" :
Two parts includes details of the history of some organic compound and organometallic complexes and gives a general introduction survey, review and new scientific background of the basic principle theory of isatin derivatives and palladium- catalyzed, cross-coupling and oxidative addition reactions including examples for the synthesis of some isatin derivatives and organopalladium complexes related to our work.
Chapter Two "Results and Discussion" :
Part (I)
Deals with a detailed study for synthesis, characterization and describes the strategy of the methods that can be applied to give products in pure form, resulting in the synthesis of a class of organic compounds by using different reagents.
It includes as well investigating the synthesis of some new heterocyclic systems from 5-methylisatin by reaction with phenyl rhodanine, 4-chlorophenyl rhodanine and rhodanine to give thioxothiazolidin derivative 101a-c and this compound treated with formaldehyde and secondary amines such as piperdine, and piperazine to give mannich base derivative 102a-i. Another piece of evidence for structure of compound 102a-i, is obtained by authentic method via the react of isatin with formaldehyde and Secondary amines to yield 103a,b then condensation of 103a,b with 3-substituted-4-thiazolidinone in presence of AcONa/ AcOH to give 102a,b. .
The compound 101a-c is reduced by Zn/ AcOH to give compound 104a-c. Which reacted with 20amine and formaldehyde to afford 105a,b. Which obtained by authentic method Via the reduction of 102g,h with Zn/ AcOH.
The 5-(5-Chloro-2-oxoindolin-3yl)-3-phenyl-2thioxothiazolidin-4-one 104c reacted with phosphorousoxychloride to give 5-(2-chloro -5-methyl - 3H -indol-3-yl) -3-(4–chlorophenyl)–2-thioxothiazolidin-4-one 107 in good yield, which reacted with different primary amines such as p- hydroxyl aniline afforded 3-(4-chlorophenyl)- 5 -(2-((4- hydroxyphenyl) amino)-5-methyl-3H-indol-3-yl)-2-thioxothiazolidin-4-one 108.
Chapter One "Introduction" :
Two parts includes details of the history of some organic compound and organometallic complexes and gives a general introduction survey, review and new scientific background of the basic principle theory of isatin derivatives and palladium- catalyzed, cross-coupling and oxidative addition reactions including examples for the synthesis of some isatin derivatives and organopalladium complexes related to our work.
Chapter Two "Results and Discussion" :
Part (I)
Deals with a detailed study for synthesis, characterization and describes the strategy of the methods that can be applied to give products in pure form, resulting in the synthesis of a class of organic compounds by using different reagents.
It includes as well investigating the synthesis of some new heterocyclic systems from 5-methylisatin by reaction with phenyl rhodanine, 4-chlorophenyl rhodanine and rhodanine to give thioxothiazolidin derivative 101a-c and this compound treated with formaldehyde and secondary amines such as piperdine, and piperazine to give mannich base derivative 102a-i. Another piece of evidence for structure of compound 102a-i, is obtained by authentic method via the react of isatin with formaldehyde and Secondary amines to yield 103a,b then condensation of 103a,b with 3-substituted-4-thiazolidinone in presence of AcONa/ AcOH to give 102a,b. .
The compound 101a-c is reduced by Zn/ AcOH to give compound 104a-c. Which reacted with 20amine and formaldehyde to afford 105a,b. Which obtained by authentic method Via the reduction of 102g,h with Zn/ AcOH.
The 5-(5-Chloro-2-oxoindolin-3yl)-3-phenyl-2thioxothiazolidin-4-one 104c reacted with phosphorousoxychloride to give 5-(2-chloro -5-methyl - 3H -indol-3-yl) -3-(4–chlorophenyl)–2-thioxothiazolidin-4-one 107 in good yield, which reacted with different primary amines such as p- hydroxyl aniline afforded 3-(4-chlorophenyl)- 5 -(2-((4- hydroxyphenyl) amino)-5-methyl-3H-indol-3-yl)-2-thioxothiazolidin-4-one 108.
Other data
| Title | Synthesis of Novel N, S-Heterocyclic Compounds via Metallacycles | Other Titles | "تشييد مركبات جديدةغير متجانسة الحلقة تحتوي علي ذرتي النتروجين و الكبريت بواسطة مركبات حلقية فلزية" | Authors | Eman Hassan Khalil Hassan | Issue Date | 2013 |
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