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CHAPTER – 1 PREPARATION AND YIELD OPTIMIZATION OF 2- METHYL INDOLINE AND STUDY OF MANNICH REACTION ON 2-METHYL INDOLINE MOIETY 1.1 Aim of current work 34 1.2 Reaction scheme 36 1.3 Plausible reaction mechanism 38 1.4 Experimental 40 1.5 Physical data tables 44 1.6 Spectral discussion 46 1.6.1 Mass spectral study 46 1.6.2 IR spectral study 49 1.6.3 1 H & 13 C NMR spectral study 49 1.6.4 Elemental analysis 53 1.7 Analytical data 53 1.8 Results and discussion 58 1.9 Conclusion 59 1.10 Spectral representation of synthesized compounds 60
Chapter – 1 Preparation and Yield optimization..... 1.1 AIM OF CURRENT WORK Since last few years, our group is involved in the synthesis of nitrogen containing heterocycles viz. pyrrole, indole, 2-methyl indole, dihydropyridine, dihydropyrimidine, 4-hydroxy quinolones etc. Where, pyrrole, indole, dihydropyridine, dihydropyrimidine, 4-hydroxy quinolone and 2-methyl indole showed good anti tubercular, anti diabetic, anti cancer and multi drug resistance reversal activity. Looking to the interesting biological profile showed by indole, 2-methyl indole and 2-methyl indoline from the literature survey and development of a simple preparation method for 2-methyl indole by our group we decided to prepare 2-methyl indoline and to explore the chemistry involving 2-methyl indoline moiety. Literature revealed that different types of N-alkylation reactions have been carried out on 2-methyl indoline which include introduction of acetyl group, introduction of chloroacetyl group and further treatment with secondary amines, formylation at N1 position and preparation of Schiff bases, preparation of amide linkages and alkylation by means of one and two carbon chains. Recently a Mannich reaction has been carried out on N1 position in 2-methyl indoline using benzotriazole and formaldehyde. Looking to the reactivity of N1 position for Mannich reaction, the secondary nitrogen is more active than C3 while in 2-methyl indole, Mannich reaction goes on both N1 and C3 positions depending upon the reaction conditions. Mannich bases can be synthesized by Mannich reaction on nitrogen of secondary amine having hydrogen atom with pronounced activity using simplified methodology and easy work up and this inspired us to develop some new N-substituted 2-methyl indoline derivatives by Mannich reaction. Literature also revealed that secondary amines viz. morpholine, piperidine, pyrrolidine, piperazine derivatives and other secondary amines like dimethylamine, diethylamine etc. and primary and secondary aromatic amines have not been used yet that is why we used primary and secondary amines to a R. Abonia, A. Albornoz, B. Insuasty, J. Quiroga, H. Meier, A. Hormaza, M. Nogueras, A. Sanchez, J. Cobo and J. N. Low; Tetrahedron, 2001, 57(23), 4933. Department of Chemistry, <strong>Saurashtra</strong> <strong>University</strong>, Rajkot-360 005 34
Page 1 and 2: Saurashtra University Re - Accredit
Page 3 and 4: Statement under O. Ph. D. 7 of Saur
Page 6 and 7: ACKNOWLEDGEMENT It is a moment of g
Page 8 and 9: Jignesh Lunagariya, Hitesh Sarvaiya
Page 10 and 11: CONTENT Content General Remarks 6 A
Page 12 and 13: Content 3.2 Reaction scheme 149 3.3
Page 14 and 15: 5.14 Conclusion 313 5.15 Spectral r
Page 16 and 17: MF Molecular Formula MW Molecular W
Page 18 and 19: GABA Gamma Amino Butyric Acid MES M
Page 20 and 21: PART - A STUDIES ON 2-METHYL INDOLI
Page 22 and 23: Part-A Studies on 2-methyl indoline
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Chapter - 2 Microwave assisted simp
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Part - B Studies on isatin derivati
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CHAPTER - 3 PREPARATION OF SMALL LI
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Chapter - 3 Preparation of small li
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CHAPTER - 4 STUDIES ON DIFFERENT TY
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Chapter - 4 Studies on different ty
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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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