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CHAPTER – 4 STUDIES ON DIFFERENT TYPES OF REACTIONS ON PYRAZOLE CORE STRUCTURE 4.1 Introduction to pyrazole aldehydes 188 4.2 Introduction to oxindole 190 4.2.1 Physical properties of oxindole 190 4.2.2 Synthesis of oxindole 191 4.2.3 Synthetic oxindoles as enzyme inhibitors 193 4.3 Introduction to coumarin 199 4.3.1 Synthesis of 4-hydroxycoumarin 199 4.3.2 Biological activities associated with 4-hydroxycoumarin derivatives 200 4.3.3 Introduction to coumarinyl chalcones 201 4.3.4 Chalcones of 3-acetyl-4-hydroyxcoumarin 205 4.4 Introduction to chromane diones 208 4.5 Use of 4-hydroxycoumarin in dihydropyrimidine synthesis 213 4.6 Aim of current work 216 4.7 Reaction scheme 218 4.8 Plausible reaction mechanism 222 4.9 Experimental 224 4.10 Physical data tables 230 4.11 Spectral discussion 235 4.11.1 Mass spectral study 235 4.11.2 IR spectral study 240 4.11.3 1 H & 13 C NMR spectral study 242 4.11.4 Elemental analysis 245 4.12 Analytical data 245 4.13 Results and discussion 252 4.14 Conclusion 253 4.15 Spectral representation of synthesized compounds 254 4.16 References 264
Chapter – 4 Studies on different types of reactions….. 4.1 INRODUCTION TO PYRAZOLE ALDEHYDES Pyrazole refers both to the class of simple aromatic ring organic compounds of the heterocyclic series characterized by a five-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions and to the unsubstituted parent compound. Being so composed and having pharmacological effects on humans, they are classified as alkaloids, although they are rare in nature. The synthesis of pyrazoles remains of great interest owing to the wide applications in pharmaceutical and agrochemical industry due to their herbicidal, fungicidal, insecticidal, analgesic, antipyretic and anti-inflammatory properties. 1, 2 Some methods have been developed in recent years, though the most important method is the reaction between hydrazines and βdicarbonyl compounds. 3 This reaction involves the double condensation of 1, 4, 5 3-diketones or α, β-unsaturated ketones with hydrazine or its derivatives. However, the appealing generality of this method is somewhat vitiated by the severe reaction conditions or the multistep sequences usually required to access the starting materials. 6 Thus, continuous efforts have been devoted to the development of more general and versatile synthetic methodologies for this class of compounds. 7 The application of Vilsmeier–Haack (VH) reagent (POCl3 / DMF) for formylation of a variety of both aromatic and heteroaromatic substrates is well documented. 8 Besides this, the reagent has also been extensively used for effecting various chemical transformations from other classes of compounds. Many of these reactions have led to novel and convenient routes for the synthesis of various heterocyclic compounds. 9 A notable example that finds significant application in heterocyclic chemistry is the synthesis of 4formylpyrazoles from the double formylation of hydrazones with Vilsmeier- Haack (VH) reagent. 10, 11 These observations, coupled with the recent developments on the simple synthesis of pyrazole derivatives, 1, 2 especially 4-functionalized 1, 3-diphenylpyrazoles as antibacterial, [12] antiinflammatory, 13, 14 antiparasitic, 15 and antidiabetic 16 drugs, prompted Department of Chemistry, <strong>Saurashtra</strong> <strong>University</strong>, Rajkot – 360 005 188
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Saurashtra University Re - Accredit
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Statement under O. Ph. D. 7 of Saur
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ACKNOWLEDGEMENT It is a moment of g
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Jignesh Lunagariya, Hitesh Sarvaiya
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CONTENT Content General Remarks 6 A
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Content 3.2 Reaction scheme 149 3.3
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5.14 Conclusion 313 5.15 Spectral r
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MF Molecular Formula MW Molecular W
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GABA Gamma Amino Butyric Acid MES M
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PART - A STUDIES ON 2-METHYL INDOLI
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Part-A Studies on 2-methyl indoline
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CHAPTER - 1 PREPARATION AND YIELD O
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Chapter - 1 Preparation and Yield o
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Chapter - 2 Microwave assisted simp
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Part - B Studies on isatin derivati
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Chapter - 5 Synthesis and Character
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Chapter - 6 Biological evaluation o
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Summary Synthesis and biological pr
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Summary Synthesis and biological pr
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Conferences / Seminar / Workshop At
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