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Thioamides, Quinolinium and Isoquinolinium Salts: Useful Synthons in the Synthesis of Heterocyclic Compounds and Asymmetric Synthesis of Sulfonic acid Derivatives
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
We have reported a new and efficient synthesis of a broad spectrum of heterotetracyclic benzoxazocines via unique tandem 1,3-dinucleophilic addition of different bifunctional nucleophiles to quinolinium and isoquinolinium salts. The reaction generally involves the initial addition of nucleophiles to quinolinium salts to form enamine intermediate which can be trapped by intramolecular O/S-alkylation of nucleophiles. This protocol is a very mild and simple method for construction of eight-membered ring in fused heterocycles in a one-step process. We have also developed an efficient asymmetric synthesis of α,β-disubstituted γ-bisalkoxycarbonyl and α, β- disubstituted γ- phosphono sulfonates via...
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
1,3-Dipolar cycloaddition reactions constitute one of the most fundamental reactions for construction of five-membered heterocyclic compounds Spiro and dispirooxindoles have become important synthetic targets as these structural frameworks form the core units of many naturally occurring molecules that possess abundant biological activities .In this report we used (E)-Aryl ideneindolinones as unusual dipolarophiles for synthesis of dispirooxindoles. In follow different bifunctional nucleophiles for example 1,3-dicarbonyl, phenol, thioindole can be used in synthesis of benzoxazocines We have reported a new and efficient synthesis of benzoxazocines via unique tandem 1,3-dinucleophilic addition...
Synthesis of Heterocyclic Compounds via Domino Knoevenagel Hetero Diels–Alder Reaction on Thiocarbonyls and Investigation of Tandem Dinucleophilic Addition on Pyridinium Salts
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
In the first chapter, three efficient synthesis of novel polyheterocyclic indole and thiochromone-annulated thiopyranocoumarin derivatives are achieved via domino Knoevenagel hetero Diels–Alder reaction of O-acrylated and O-propargylated salicylaldehyde derivatives with indolin-2-thiones and 4-hydroxy dithiocoumarin. The domino Knoevenagel-hetero-Diels–Alder reactions are very efficient process that allows the formation of two or more rings at once, avoiding sequential chemical transformations. The products are formed in good-to-excellent yields with high regio- and stereoselectivity. The major advantage of this reaction is the ease of the work-up during which the products can be isolated...
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
We have reported a new and efficient synthesis of a broad spectrum of heterotetracyclic benzoxazocines via unique tandem 1,3-dinucleophilic addition of different bifunctional nucleophiles to quinolinium and isoquinolinium salts. The reaction generally involves the initial addition of nucleophiles to quinolinium salts to form enamine intermediate which can be trapped by intramolecular O/S-alkylation of nucleophiles. In the third part, as continues, we have reported another method which consists of Anthocyanidins and Thioindoles by using water and acetic acid as the solvent. This protocol is a very mild and simple method for construction of eight-membered ring in fused heterocycles in a...