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TITLE
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
DEDICATION
CONTENTS
1. CHLOROMETHYLENEIMINIUM SALTS: METHODS OF GENERATION AND APPLICATIONS
1.1 INTRODUCTION
1.2 REACTIONS OF CHLOROMETHYLENEIMINIUM SALTS WITH TERTIARY ALCOHOLS
1.3 CHLOROMETHYLENEIMINIUM SALTS: REACTIONS WITH ALKENES
1.4 REACTIONS OF CARBINOLS DERIVED FROM ACYL KETENEDITHIOACETALS
1.5 CHLOROMETHYLENEIMINIUM SALTS: REACTIONS WITH CARBONYL COMPOUNDS
1.5.1 Reactions of Acyclic Ketones with Chloromethyleneiminium Salts
1.5.2 Reactions of Cyclic Ketones with Chloromethyleneiminium Salts
1.5.3 Reactions of α, β-Unsaturated Acyclic Ketones with Chloromethyleneiminium Salts
1.5.4 Reactions of α, β-Unsaturated Cyclic Ketones with Chloromethyleneiminium Salts
1.5.5 Reactions of Acyclic 1, 3-Diketones with Chloromethyleneiminium Salts
1.5.6 Reactions of Cyclic 1, 3-Diketones with Chloromethyleneiminium Salts
1.6 IMINIUM SALT MEDIATED SYNTHESIS OF PYRIDINES
1.7 REACTIONS OF TERTIARY ALCOHOLS WITH VILSMEIER REAGENT FOLLOWED BY AMMONIUM ACETATE: SYNTHESIS OF FUNCTIONALIZED PYRIDINES AND NAPHTHYRIDINES
1.7.1 Reactions of 2-Aryl-2 propanols with Chloromethyleneiminium Salt Followed by Ammonium Acetate
1.7.2 Reaction of 2 Methyl-4 phenyl-3-buten-2-ol with Chloromethyleneiminium Salt Followed by Ammonium Acetate
17.3 Reactions of 2-Aryl-2-butanols with Chloromethyleneiminium Salt Followed by Ammonium Acetate
1.7.4 Reactions of Aliphatic and Alicyclic Alcohols with Chloromethyleneiminium Salt Followed by Ammonium Acetate
1.8 REACTIONS OF α-HYDROXYKETENEDITHIOACETALS WITH CHLOROMETHYLENEIMINIUM SALT FOLLOWED BY AMMONIUM ACETATE: SYNTHESIS OF 4-ARYL-2 (METHYLSULFANYL) PYRIDINES
1.9 REACTIONS OF CARBONYL COMPOUNDS WITH CHLOROMETHYLENEIMINIUM SALT FOLLOWED BY AMMONIUM ACETATE: SYNTHESIS OF SUBSTITUTED PYRIDINES
1.10 CONCLUSIONS
1.11 REFERENCES
2. VILSMEIER-HAACK REACTIONS OF TERTIARY ALCOHOLS: SYNTHESIS OF FUNCTIONALIZED PYRIDINES AND NAPHTHYRIDINES
2.1 INTRODUCTION
2.2 GENERAL METHODS FOR THE PREPARATION OF FUNCTIONALIZED PYRIDINES
2.3 RESULTS AND DISCUSSION
2.3.1 Reactions of 2-Aryl-2 propanols with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.3.2 Reaction of 2 Methyl-4 phenyl-3-buten-2-01 with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.3.3 Reactions of 2 Aryl-2-butanols with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.4 REACTIONS OF ALIPHATIC AND ALICYCLIC TERTIARY ALCOHOLS WITH CHLOROMETHYLENEIMINIUM SALT: SYNTHESIS OF FUNCTIONALIZED NAPTHYRIDINES
2.4.1 Reaction of tent-Rutanol with Chloromethyleneimmium Salt Followed by Ammonium Acetate
2.4.2 Reaction of 2 Methyl-2-butanol with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.4.3 Reaction of 3 Methyl-3 pentanol with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.4.4 Reaction of 1-Methyl-1-cyclohexanol with Chloromethyleneiminium Salt Followed by Ammonium Acetate
2.5 CONCLUSIONS
2.6 EXPERIMENTAL
2.6.1 General Procedure for the Preparation of 2-Aryl-2 propanols from Substituted Acerophenones
2.6.2 Reactions of Substituted 2-Aryl-2 propanols with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 4 Arylnicotinaldehydes
2.6.3 Reaction of 2-Methyl-0 phenyl-3-buten-2-ol with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 4- (Phenyl vinyl) nlcotinaldehyde
2.6.4 Preparation of 2 Aryl-2-butanols: General Procedure
2.6.5 Reactions of 2 Aryl-2-butanols with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 4Aryl-5-methylnicotinaldehydes
2.6.6 General Procedure for the Preparation of Aliphatic and Alicyclic Tertiary Alcohols from Ketones
2.6.7 Reactions of Aliphatic and Alicyclic Tertiary Alcohols with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of Substituted [2, 7]Naphthyridines
2.7 REFERENCES
3. REACTIONS OF FUNCTIONALIZED KETENEDITHIOACETALS WITH VILSMEIER REAGENT: SYNTHESIS OF ARYL ALKYLTHIOPYRIDINES
3.1 INTRODUCTION
3.2 α-OXOKETENEDITHIOACETALS: SYNTHESIS
3.3 α-OXOKETENEDITHIOACETALS: REACTIVITY
3.3.1 Synthesis of Pyridines from Ketenedithioacetals: General Methods
3.3.2 Synthesis of Alkylthio Pyridines: Alternative Approaches
3.4 RESULTS AND DISCUSSION
3.4.1 Reactions of 2-Aryl-4, 4-bis (methylsulfanyl) -3-buten-2-ols with Chloromethyleneiminium Salt f allowed by Ammonium Acetate
3.5 CONCLUSIONS
3.6 EXPERIMENTAL
3.6.1 General Procedure for the Preparation of α-Hydroxy ketenedithioacetals from α-Oxoketenedithioacetals
3.6.2 Reactions of α-Hydroxy ketenedithioacetals with Vilsmeier Reagent Followed by Ammonium Acetate; Synthesis of 4 Aryl-2- (methylsulfanyl) pyridines
3.7 REFERENCES
4. REACTIONS OF CARBONYL COMPOUNDS WITH CHLOROMETHYLENEIMINIUM SALTS: SYNTHESIS OF SUBSTITUTED PYRIDINES
41 INTRODUCTION
4.2 GENERAL METHODS FOR THE SYNTHESIS OF CHLOROSUBSTITUTED PYRIDINECARBOXALDEHYDES AND RELATED COMPOUNDS
4.3 GENERAL METHODS FOR THE SYNTHESIS OF SUBSTITUTED PYRIDINES
4.4 THE REACTIVITY OF BENZYL METHYL KETONES TOWARDS ELECTROPHILIC REAGENTS
4.5 RESULTS AND DISCUSSION
4.5.1 Reactions of 1 Aryl-2 propanones with Chloromethyleneiminium Salt Followed by Ammonium Acetate
4.5.2 Reaction of Benzyl Ethyl Ketone with Chloromethyleneiminium Salt Followed by Ammonium Acetate
4.5.3 Reaction of Dibenzyl Ketone with Chloromethyleneiminium Salt Followed by Ammonium Acetate
4.5.4 Reaction of Acyl Ketenedithioacetal with Chloromethyleneiminium Salt Followed by Ammonium Acetate
4.6 CONCLUSIONS
4.7 EXPERIMENTAL
4.7.1 Reactions of Substituted Phenyl Acetones with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 5-Aryl-4-chloronicotinaldehydes
4.7.2 Reaction of 1-Phenyl-2-butanone with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 4-Chloro-3-methyl-5 phenylpyridine
4.7.3 Reaction of Dibenzyl Ketone with Vilsmeier Reagent Followed by Ammonium Acetate Synthesis of 3, 5-Biphenyl-4- (N, N-dimethylamino) pyridine
4.7.4 Reaction of 4, 4-Bis (methylsulfanyl) -3 phenyl-3-buten-2-one with Vilsmeier Reagent Followed by Ammonium Acetate: Synthesis of 4-Chloro-2- (methylsulfanyl) -3 phenylp vridine
4.8 REFERENCES