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Chapter – 5 Synthesis and Characterization….. 5.8.3 GENERAL PROCEDURE FOR THE PREPARATION OF DNJ-1001 TO DNJ-1015 0.01 mole of appropriately substituted aryl amino coumarin was dissolved into 30 ml of dimethylformamide. 1 ml of formaldehyde (37-41 % solution) and 0.01 mole of an appropriate secondary amine were added into above reaction mixture under acidic condition. The content was heated on boiling water bath for some time and the reaction mixture was left overnight at room temperature to furnish the product. The separated crystals were filtered off and it was washed with acetone to give white to pale yellow coloured shining crystals. The purity of the compound was checked by silica gel-G F254 thin layer chromatography using toluene : ethyl acetate (7 : 3) as a mobile phase. Recrystallization was not required in any case though it was carried out from acetone / methanol. (Physical data of the synthesized end products are summarized in the table 5.9.1) 1-methyl piperazine was used in case of DNJ-1001 while 1-benzyl piperazine was used in case of DNJ-1003. Rests of the compounds were synthesized using 1-ethyl piperazine. Moreover single crystal of DNJ-1003 was developed in order to prove the X-ray crystallographic structure. Acquired crystal structure and related data are also given. Department of Chemistry, Saurashtra University, Rajkot – 360 005 295
Chapter – 5 Synthesis and Characterization….. 5.9 PHYSICAL DATA TABLES 5.9.1 Physical data of 4-(substituted aniline) coumarins C-Mannich bases (DNJ-1001 to DNJ-1015) Substitution Code R1 & R2 R3, R4 & R5 DNJ 1001 DNJ 1002 DNJ 1003 DNJ 1004 DNJ 1005 DNJ 1006 DNJ 1007 DNJ 1008 DNJ 1009 DNJ 1010 DNJ 1011 1-methyl piperazinyl 1-ethyl piperazinyl 1-benzyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl 1-ethyl piperazinyl R 5 R 4 Department of Chemistry, Saurashtra University, Rajkot – 360 005 296 O MF O NH N R1 R 3 R 2 MW (g/m) MP (°C) Rf % Yield Anilino C21H23N3O2 349 158 0.40 70 Anilino C22H25N3O2 363 164 0.43 65 Anilino C27H27N3O2 425 176 0.50 63 2-chloro phenyl amino C22H24ClN3O2 397 170 0.44 59 3-chloro phenyl amino C22H24ClN3O2 397 168 0.46 61 4-chloro phenyl amino C22H24ClN3O2 397 162 0.48 55 2-fluoro phenyl amino C22H24FN3O2 381 184 0.42 46 4-fluoro phenyl amino C22H24FN3O2 381 190 0.44 58 2-methyl phenyl amino C23H27N3O2 377 180 0.44 67 3-methyl phenyl amino C23H27N3O2 377 186 0.46 63 2-methoxy phenyl amino C23H27N3O3 393 174 0.45 44
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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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