Synthesis and Characterization of Some New N-saccharin Derivatives Aseel Farhan Abdullah Prof ... PDF
Preview Synthesis and Characterization of Some New N-saccharin Derivatives Aseel Farhan Abdullah Prof ...
Ministry of Higher Education and Scientific Research University of Baghdad College of Science Department of Chemistry Synthesis and Characterization of Some New N-saccharin Derivatives A Thesis R Submitted to the College of Science University of Baghdad in Partial Fulfillment of the Requirements for the Degree of Master of Science in Organic Chemistry By Aseel Farhan Abdullah B.Sc.Chemistry,College of Science Baghdad University(2003) Supervised by Prof.Dr.Ahmed W.Naser 2014 A.D. 1435 A.H. ﻢِﻴﺣﺮﻟﺍ ِﻦﻤﺣﺮﻟﺍ ِﺍ ِﻢﺴِﺑ ﴿ ﺎﻨَﺘﻤﱠﻠﻋ ﺎﻣ ﺎﱠﻟِﺇ ﺎﻨَﻟ ﻢْﻠﻋ ﺎَﻟ ﻚَﻧﺎﺤﺒﺳ ﺍﻮُﻟﺎَﻗ ﴾ ﻢﻴﻜﺤْﻟﺍ ﻢﻴﻠﻌْﻟﺍ ﺖْﻧَﺃ ﻚﱠﻧِﺇ 32 ءﺍﺪﻫﻹﺍ (ﻞﺟﻭ ﺰﻋ) ﷲﺍ ... (ﻢﻠﺳﻭ ﻪﻟﺍﻭ ﻪﻴﻠﻋ ﷲﺍ ﻰﻠﺻ) ﺪﻤﳏ ﻢﻳﺮﻜﻟﺍ ﻝﻮﺳﺮﻟﺍ ... (ﷲﺍ ﻪﲪﺭ) ﻱﺪﻟﺍﻭ .... ﻲﺗﺪﻟﺍﻭ .... ﺽﺎﻳﺭ ﻲﺟﻭﺯ.... ﻲﺗﺍﻮﺧﺃﻭ ﻲﺧﺃ.... ﻲﺋﺎﻨﺑﺍ.... ﻞﺿﺎﻓﻻﺍ ﻲﺗﺬﺗﺎﺳﺃ.... ﺮﻳﺪﻘﺗﻭ ﺮﻜﺷ ﻩﺎﻳﺎﻄﻋ ﺄـﻓﺎﻜﻳ ﺎﻤﺑ ءﺎـﻓوو اﻮﻔﻋو اﺪﻋو قﺪﺻﻻا ءﺎﻋﺪﻟا ﺐﻴﺠﻣ ﻪﻟ ﺮﻜﺸﻟاو ﷲ ﺪﻤﺤﻟا ﻰﻠﻋو ﻪﻴﻠﻋ ﷲا ﻰﻠﺻ) ﺪﻤﺤﻣ ﻰﻔﻄﺼﻤﻟا ﺐﻴﺒﺤﻟا ﻰﻠﻋ مﻼﺴﻟاو ةﻼﺼﻟا ﻢﺗاو .دازو ءﺎﺷ ﺎﻤﺑو ﺔﻨﻃﺎﺑو ةﺮﻫﺎﻇ ﷲا ﻢﻌﻧ دﺪﻌﺑ( رﺎﻬﻃﻻا ﻦﻴﺒﻴﻄﻟا ﻪﻟا ﻢﻜﻳﺪﻳا ﻦﻴﺑ اﺬﻫ يﺪﻬﺟ ﻊﺿا نا ﻰﻟا ﻰﻟﺎﻌﺗو ﻪﻧﺎﺤﺒﺳ ﷲا ﻲﻨﻘﻓو ﺪﻘﻟ ﺪﻌﺑ ﻖﺤﻟا ﻢﺛ .ﺮﻴﺧ ﻰﻠﻋ ﻪﻤﺗا يﺬﻟا ةﺰﻌﻟا بر ﷲا ﻞﻀﻓ ﻪﻟوا ﻲﻓ ةﺮﻛاذ .د. أ ﻞﺿﺎـﻔﻟا يذﺎﺘﺳا ﻰﻟا ﻲﻧﺎﻨﺘﻣا ﻢﻴﻈﻋو يﺮﻜﺷ ﻞﻳﺰﺟ ﻞﺠﺳا نا ﻖﺤﻟا ﻪﺳﺮﻛ ﺎﻤﻟ ﺔﻟﺎﺳﺮﻟا ﻩﺬﻫ ﻰﻠﻋ فاﺮﺷﻷﺎﺑ ﻞﻀﻔﺗ يﺬﻟا ﺮﺻﺎﻧ ﺪﻴﺣو ﺪﻤﺣأ ﻪﺑ ﻊﺘﻤﺗ يﺬﻟا ﺮﺒﺼﻟاو ﺔﺼﻠﺨﻣو ﺔﻨﻴﻣا حورو ﻪﻴﻓاو ﻪﻌﺑﺎﺘﻣو ﻞﻳﻮﻃ ﺖﻗو ﻦﻣ ﺎﻤﻛ .ﺪﻳﺪﻤﻟا ﺮﻤﻌﻟاو ﺔﺤﺼﻟﺎﺑ ﻪﺘﻠﺋﺎﻌﻟو ﻪﻟ ﷲا ﻦﻣ ﺔﻴﻋاد ﻲﻟ ﻪﻌﻴﺠﺸﺗو ءﺎﻴﻤﻴﻜﻟا ﻢﺴﻗ ﻲﻓ ﻞﺿﺎـﻓﻻا ﻲﺗﺬﺗﺎﺳا ﻊﻴﻤﺟ ﻰﻟا ﻞﻳﺰﺠﻟا ﺮﻜﺸﻟا مﺪﻗا ﺖﺴﻟا ﻰﻟاو ءﺎﻴﻤﻴﻜﻟا ﻢﺴﻗ ﺔﺳﺎﺋر ﻰﻟا ﺮﻜﺸﻟا مﺪﻗاو .ﻢﻬﻌﻴﺠﺸﺗو ﻢﻬﻧوﺎﻌﺘﻟ ﻞﻴﻟﺎﺤﺘﻟا زﺎﺠﻧا ﻲﻓ ﺔﻟوﺬﺒﻤﻟا ﺎﻫدﻮﻬﺠﻟ ﻲﻣﺪﺨﻟا ﺮﺒﺘﺨﻤﻟا ﻲﻓ ةﺮﻴﻨﻣ .ﺔﻴﻔﻴﻄﻟا ارﺬﻌﻓ ﻢﻬﻨﻋ لﺎﺒﻟا ﻞـﻔﻏ ﻦﻣو ﻢﻬﺗﺮﻛذ ﻦﻣ ﻊﻴﻤﺟو ﻲﺘﻠﺋﺎﻌﻟ اﺮﻜﺷ اﺮﻴﺧاو ﻲﻓ تﺎﺒﻴﻄﻟا ﻦﻣ ﻢﻜﻗزرو ﷲا ﻢﻛﺎﻤﺣ يﺮﺧذو يﺪﻨﺳ ﺎﻌﻴﻤﺟ ﻢﺘﻧا ،ﻢﻬﻟ .ﻲﻠﻋ ﻢﻜﻠﻀﻓ ﻦﻣ اءﺰﺟ ﻮﻟو درﻷ ﻲﻨﻘﻓﻮﻳ نا ﻩﻮﻋداو ةﺮﺧﻻاو ﺎﻴﻧﺪﻟا ﷲاﺪﺒﻋ نﺎﺣﺮﻓ ﻞﻴﺳأ......ﻖﻴﻓﻮﺘﻟا ﻲﻟو ﷲاو Supervision Certificate I certify that this thesis was prepared under my supervision at the University of Baghdad, College of Science as a partial requirement for the degree of Master in Chemistry. Signature: Supervisor: Dr. Ahmed Wahed Nasir Title: Professor Address: Department of Chemistry-College of Science-Baghdad University Date: / / 2014 In view of the available recommendations, I forward this thesis for debate by the examination committee. Signature: Name: Prof. Dr. Mohammed R. Ahmed Chairman of Chemistry Department College of Science Baghdad University Date: / / 2014 Contents NO. Subject Pages CHAPTER ONE:INTRODUCTION 1-1 Heterocyclic compounds 1 1-2 Schiff bases 1 1-3 B-Lactam 5 1-4 Oxazepine 10 1-5 Thiazole 13 1-6 Oxazole 17 1-7 Oxazoline 19 1-8 The aim of the work 20 CHAPTER TWO:EXPERIMENTAL PART 2-1 Apparatus and Material 21 2-2 Synthesis of Ethyl- α-(N-saccharin)acetate[1] 22 2-3 Synthesis of N-(amino carbonthioyl)-α-(N- 22 saccharin)acetamide[2] 2-4 Synthesis of N-(amino carbonyl)-α-(N-saccharin) 22 acetamide[3] 2-5 Synthesis of α-(N-saccharin)acetohydrazide[4] 22 2-6 Synthesis of 1,3-thiazole derivatives[5,6] 23 2-7 Synthesis of 1,3-oxazole derivatives[7,8] 23 2-8 Synthesis of carboxamide derivatives[9,10] 24 2-9 Synthesis of oxazoline derivatives[11-14] 25 2-10 Synthesis of imides derivatives[15-17] 26 2-11 Synthesis of Schiff bases derivatives[18-20] 28 2-12 Synthesis of azetidine derivatives[21-23] 29 2-13 Synthesis of oxazepine derivatives[24-32] 30 CHAPTER THREE:RESULTS AND DISCUSSION 3-1 Ester and hydrazide derivatives[1,4] 32 3-2 Synthesis of N-(amino carbonyl)-α-(N-saccharin) 35 acetamide[3] 3-3 Synthesis of N-(amino carbon thioyl)-α-(N- 35 saccharin)acetamide[2] 3-4 Synthesis of 1,3-thiazole derivatives[5,6] 36 3-5 Synthesis of 1,3-oxazole derivatives[7,8] 43 3-6 Synthesis of carboxamides derivatives[9,10] 46 3-7 Synthesis of oxazoline derivatives[11-14] 46 I 3-8 Synthesis of imide derivatives[15-17] 56 3-9 Synthesis of Schiff bases[18-20] 62 3-10 Synthesis of azetidine -2-one derivatives[21-23] 67 3-11 Synthesis of oxzazepine derivatives[24-32 73 3-12 Future work 86 List of schemes Subject page Scheme1:Mechanism of [5,6]synthesis 36 Scheme2:Mechanism of [9,10]synthesis 46 Scheme3:Mechanism of [11-14]synthesis 47 Scheme4:Mechanism of [15-17]synthesis 56 Scheme5:Mechanism of [21-23]synthesis 67 Scheme6:Mechanism of [24-32]synthesis 73 List of Tables NO. Title of Table page 3-1 Characteristic FT.IR absorption bands of 32 compounds 1 and 4 3-2 Characteristic FT.IR absorption bands of 36 compounds 3 and 2 3-3 Characteristic FT.IR absorption bands of 37 compounds 5 and 6 3-4 Characteristic FT.IR absorption bands of 43 compounds 7 and 8 3-5 Characteristic FT.IR absorption bands of 48 compounds [11-14] 3-6 Characteristic FT.IR absorption bands of 57 compounds [15-17] 3-7 Characteristic FT.IR absorption bands of the B- 68 lactam derivatives [21-23] 3-8 Characteristic FT.IR absorption bands of oxazepine 74 derivatives [24-32] II List of Figures No. Title of Figures Pages 1 FT.IR spectrum of compound[1] 33 2 FT.IR spectrum of compound[4] 34 3 FT.IR spectrum of compound[2] 38 4 FT.IR spectrum of compound[3] 39 5 FT.IR spectrum of compound[5] 40 6 FT.IR spectrum of compound[6] 41 7 H-NMR spectrum of compound[6] 42 8 FT.IR spectrum of compound[8] 44 9 H-NMR spectrum of compound[7] 45 10 FT.IR spectrum of compound[9] 49 11 FT.IR spectrum of compound[10] 50 12 FT.IR spectrum of compound[11] 51 13 FT.IR spectrum of compound[12] 52 14 FT.IR spectrum of compound[13] 53 15 FT.IR spectrum of compound[14] 54 16 H-NMR spectrum of compound[14] 55 17 FT.IR spectrum of compound[15] 58 18 FT.IR spectrum of compound[16] 59 19 FT.IR spectrum of compound[17] 60 20 H-NMR spectrum of compound[15] 61 21 FT.IR spectrum of compound[18] 63 22 FT.IR spectrum of compound[19] 64 23 FT.IR spectrum of compound[20] 65 24 H-NMR spectrum of compound[20] 66 25 FT.IR spectrum of compound[21] 69 26 FT.IR spectrum of compound[22] 70 27 FT.IR spectrum of compound[23] 71 28 H-NMR spectrum of compound[22] 72 29 FT.IR spectrum of compound[24] 75 30 FT.IR spectrum of compound[25] 76 31 FT.IR spectrum of compound[26] 77 32 FT.IR spectrum of compound[27] 78 33 FT.IR spectrum of compound[28] 79 34 FT.IR spectrum of compound[29] 80 III 35 FT.IR spectrum of compound[30] 81 36 FT.IR spectrum of compound[31] 82 37 FT.IR spectrum of compound[32] 83 38 H-NMR spectrum of compound[26] 84 39 H-NMR spectrum of compound[28] 85 List of Abbreviations Abbreviation Phrase D.M.F Dimethylformamide % Percentage °C Centigrade Et N,TEA Triethylamine 3 R R Ar Aryl M.P Melting point R Rate of Flow f R Hrs. Hours TLC Thin Layer Chromotography FT-IR Fourier Transform Infra-red 1H-NMR Proton Nuclear Magnetic Resonance P P s Singlet d Doublet m Multiplet Heat Abs. Absolute IV Summary U Throughout this work, Thirty two of new (N-saccharin) derivatives have been synthesized from ethyl (N-saccharin) acetate [1] as a starting material. This work is divided into Two parts : the reaction steps for each part are summarized as shown below. First part: This part involves: A) Synthesis of 1,3 – thiazole [5, 6] and 1,3 –oxazole [7, 8] derivatives via the cyclization of compounds N- (aminocarbonyl) - -(N-saccharin) acetamide [2] and N- (aminothiocarbonyl)- -(N- saccharin) acetamide ∝ [3] with p-bromophenacyl bromide and p-phenylphenacyl ∝ bromide.Scheme[1] B) Synthesis of 1,3 – oxazoline derivatives [11-14] via the reaction of compound - (N- saccharin) acetohydrazide [4] with phenylisocynate and 1- naphthylisocynate and cyclization of the resulted products with p- ∝ boromophenacyl bromide and p-phenylphenacyl bromide.Scheme[1] C) Synthesis of cyclicimide derivatives [15-17] via the reaction of compound - (N- saccharin) acetohydrazide [4] with some acid anhydride, such as maleic anhydride, succinic anhydride and phthalic ∝ anhydride.Scheme[1] V
Description:The list of books you might like
