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TITLE
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
CONTENTS
1. INTRODUCTION
1.1 Reactions of polyvinyl and N-methyl pyrrolidone bromine complexes with dithioacetals and ketene dithioacetals
1.2 Studies on functionalized ketene-N, S-acetals: Facile synthesis of substituted pyrollothiazoles
1.3 Synthesis of functionalized pyrroles
1.4 Total synthesis of selected pyrrole containing marine natural products
References
2. ADVANCES IN PYRROLE SYNTHESIS: A REVIEW
2.1 Introduction
2.2 Paal-Knorr synthesis
2.3 Knorr synthesis
2.4 van Leusen synthesis
2.5 Barton-Zard reaction
2.6 Hantzsch synthesis
2.7 1, 3-Bielectrophiles in synthesis of pyrroles
2.8 Other cyclization and cycloaddition reactions
2.9 Pyrrols from functionalized azides
2.10 Recent developments
References
3. REACTIONS OF POLYVINYL AND N-METHYL PYRROLIDONE BROMINE COMPLEXES WITH DITHIOACETALS AND KETENE DITHIOACETALS
3.1 Introduction
3.2 Polymer- supported halogen complexes
3.3 General methods for the synthesis of thiolesters
3.4 Results and Discussion
3.4.1 Partial hydrolysis of α-oxoketenedithioacetals to thiolesters using bromine complexed on polyvinyl pyrrolidone
3.4.2 Deprotection of dithioacetals and dithioketals
3.4.3 Bromine in N-methyl 2-pyrrolidone: a new selective brominating reagent
3.5 Experimental
3.5.1 General procedure for the preparation of β-oxothiolcarboxylates 35 and 37
3.5.2 General procedure for the dethioacetalization
3.5.3 Bromination of 3, 3-bis (methylsulfanyl) -1-aryl-2-propen-1-one
References
4. STUDIES ON FUNCTIONALIZED KETENE-
4.1 Introduction
4.2 Preparative methods for β-oxodithioesters
4.3 Preparative methods for β-oxothioamides
4.4 Preparative methods for α-oxoketene-S, N-acetals
4.5 Ketene N, S-acetal mediated synthesis of functionalized thiazoles
4.6 Results and Discussion
4.6.1 Synthesis of alkyl 2-
4.6.2 Synthesis of alkyl 2- (E) -3 -aryl-1- (alkylsulfanyl) -3-oxo-1-propenylamino) acetate
4.6.3 Reaction of β-oxothioamides with phenacyl bromide
4.6.4 Reactions of β-oxothioamides with ethyl bromoacetate
4.6.5 Cyclization of alkyl-2-2- (z) -oxo (aryl) ethylidene-4-aryl-1, 3-thiazol-3-yl) acetate 63: Synthesis of functionalized pyrrolothiazoles
4.7 Experimental
4.7.1 General procedure for the synthesis of alkyl 2-I (3-oxo-3-arylpropanthioyl) arnino/acetate 55
4.7.2 General procrdure for the synthesis of alkyl 2- (E) -3-aryl-I- (ulkylsulfanyl) -3.-oxo-1-propenyI/ amino/acetate 61
4.7.3 General procedure for the synthesis of alkyl-2-{2- (Z) -oxo (aryl) ethylidene/-4-aryl-1, 3-thiazol-3-yl acetate 63
4.7.4 General procedure for the synthesis of ethyl-2-{4-oxo2-[ (Z) -oxo (aryl) ethylidene/-I, thiazolan-3-yl acetate 66
4.7.5 General procedure for the reaction of alkyl -2- (2-/ (z) - oxo (aryl) ethylidene|-4-aryl-1, 3-thiazol-3-yl) acetate 63 with acetic acid
4.7.6 Reaction of alkyl-2-{2-/ (Z) -oxo (aryl) ethylidene]-4-aryl-l, 3-thiazol-3-yl acetae 63 with acetic anhydride
References
5. Synthesis of Functionalized Pyrroles
5.1 Introduction
5.2 lminiurn Salt Mediated Heterocyclic Synthesis: An Overview
5.2.1 Vilsmeier-Haack Reactions of Alkenes
5.2.2 Reactions of carbonyl Compounds with Chloromethyleneiminium salts
5.2.3 Cyclization of nitriles
5.2.4 Cyclization of amides and aminoacetals
5.3 Results and [) iscussion
5.3.1 Cyclizations of β-oxoketene-N, S-acetals 62 using Vilsmeier-Haack reagent
5.3.2 Base catalyzed cyclization of β-oxoketene-N, S-acetals 62
5.4 Experimental
5.4.1 General procedure for the synthesis of alkyl 3-aryl-4-formyl-5- (alkylsulfanyI) -I H-pyrrole-2-carboxylates
5.4.2 General procedurce for the base catalyzed cyclization of β-oxoketene-N, S acetals 62
5.4.3 General procedure for the partial hydrolysis of alkyl 2-{[ (E) -aryl-I- (ethyl sulfanyl) -3-oxo-I-propenyl|amino acetate 62
References
6. Total synthesis of selected pyrrole containing marine natural products
6.1 Introduction
6.2 Total synthesis of lamellarin O and related related alkaloids: An overview
6.2.1 Furstner synthesis
6.2.2 Banwells Method
6.2.3 Wong s Method
6.2.4 Boger Synthesis
6.2.5 Bullington Synthesis
6.2.6 Guptons Method
6.3 Results and Discussions
6.3.1 Total synthesis of lamellarn O. lamellarn Q. and lukianol A
6.3.2 Efforts on a total synthesis of rigidin
6.4 Experimental
6.4.1 Genral procedure the synthesis of dithioesters 45
6.4.2 General procedure for the synthesis of β-oxothioamides 46
6.4.3 General procedure for the synthesis of ketene N, S-acetals 47
6.4.4 General Procedure for the Synthesis of 3, 4-DiarylpyrrolecarboxyIate 48
6.4.5 General procedure for reductive dethiomethylation of pyrrole 48 using Raney-NL
6.4.6 General procedure for the preparation of ketene S, N-acetal 53
6.4.7 General procedure for the preparation of thioamide 58
6.4.8 Reaction of β-oxoketene S-S-acetal 59 with sodium ethoxide
6.4.9 General Procedure for the synthesis of 6-Anilino-5-benzoyl-1, 3-dibenzyl-2, 4 (I H.3H) -pyrimidinedione 62
References