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Chapter – 5 Synthesis and Characterization….. coumarin and treatment of 4-chloro derivative with primary and secondary amines gave title compounds with weak psychotropic activity. (Fig. 5.12) O O R N 1 2 Fig. 5.12 O O Where R = MeNH, BuNH, PhCH2NH, PhNH, Me2N, Et2N, pyrrolidino, piperidino, morpholino, 4-methylpiperazino. Department of Chemistry, Saurashtra University, Rajkot – 360 005 289 R N
Chapter – 5 Synthesis and Characterization….. 5.5 AIM OF CURRENT WORK Our group is involved in the synthesis of aryl amino coumarins since last few years, where, aryl amino coumarins showed good antitubercular activity. Previously, preparation of differently substituted aryl amino coumarins was only the aim. Afterwards, the aryl amino coumarins were further cyclized to give fused pyridine as well as fused benzothiazine derivatives, which showed good antitubercular as well as anticancer activity. Looking to the interesting biological profile showed by coumarin benzothiazine derivatives and their unexplored chemistry part and from the literature survey, it was decided to modify previously prepared fused benzothiazines derived from aryl amino coumarins into N-substituted benzothiazine derivatives so that Nalkylation was carried out on coumarin benzothiazine derivatives by different methods but it failed. Then N-alkylation was carried out on aryl amino coumarin derivatives but it also failed. Afterwards, new route was thought by which benzothiazine derivatives could be synthesized that is why the Mannich reaction was carried out on aryl amino coumarins in order to prepare N- Mannich bases of aryl amino coumarins and their further cyclization into benzothiazine derivatives. But to our surprise, the Mannich reaction on aryl amino coumarin resulted into unusual new product formation which has been discussed in results and discussion in detail. Literature revealed that Mannich reaction is not reported on aryl amino coumarins but similar kind of scaffold is reported 60 . Where Mannich reaction was carried out on 4-hydroxy coumarin and the hydroxyl group present at 4 th position in coumarin nucleus was converted into chloro which was easily removed by the treatment of aromatic primary amine. As discussed in chapter – 1, Mannich bases can be synthesized by Mannich reaction on nitrogen of secondary amine by using simplified methodology and easy work up and this inspired us to develop some new aryl amino coumarin derivatives by Mannich reaction for our targeted work. Formaldehyde solution (37-41 %) and different type of secondary amines were used to acquire Mannich bases under acidic Department of Chemistry, Saurashtra University, Rajkot – 360 005 290
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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 - 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 - 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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