本論文分成兩個部分，第一部分是關於在苄基上進行C-H氧化反應，此類的化學反應在合成應用上具有廣大的用途。然而我們發現利用三價碘試劑PIDA、三氟醋酸和醋酸混合反應下產生的中間體，可以在苄基上進行C-H氧化反應，並且探討其反應機構，推測反應過程不經過單電子轉移的機制。接著針對三個反應物進行混合比例的研究，最後找到的比例是PIDA:TFA:AcOH (6:4:2)。我們也嘗試在不同的化合物之下進行苄基C-H氧化反應，但是我們發現具有對位甲氧基的化合物，才能有效的進行反應。第二部份是探討三唑化合物對生物上的影響。我們成功的先合成出具有三唑-三吡咯化合物，接著利用DNA熔點實驗、螢光取代反應實驗以及足跡分析實驗來進行三唑-三吡咯化合物對DNA的研究。我們發現三唑-三吡咯化合物確實能穩定DNA的結構。

There are two parts in this dissertation. Part I : benzylic C-H oxidation of methyl aromatic compounds is a useful reaction. We found that the reactive intermediate was generated by PIDA/TFA/AcOH (6:4:2) system then the reaction of methyl aromatic with the reactive intermediate could undergo benzylic C-H oxidation and studied on the mechanism via the intermediate. We anticipated this reaction without undergoing SET process. The benzylic C-H oxidation of p-methoxy toluene was effective in para electron-donating groups. Part II : we have synthesized a series of triazole-tripyrrole compound and studied on the binding affinity for duplex DNA by CT-DNA melting temperature analysis, ethidium bromide displacement assay for CT-DNA and DNase I footpring studies on HexA and HexB.

PART I-C-H OXIDATION WITH HYPERVALENT IODINE (III) AT BENZYLIC POSITION WITHOUT UNDERGOING SET(SINGLE ELECTRON TRANSFER) 1
1. CHAPTER ONE-REVIEW OF HYPERVALENT IODINE COMPOUND 1
1.1. INTRODUCTION 1
1.1.1. Λ3-IODINE COMPOUNDS 2
1.1.2. Λ3-IODONIUM SALTS 20
1.1.3. Λ5-IODINE COMPOUNDS (IODINE(V) COMPOUND) 25
1.2. REFERENCE 28
2. CHAPTER TWO-BENZYLIC C-H OXIDATION 36
2.1. INTRODUCTION 36
2.1.1. OXIDATION AT BENZYLIC CARBON CENTER WITH IBX AFFORD ALDEHYDE OR KETONE 38
2.1.2. OXIDATION OF PARA-METHYL ANISOLE TO ACID 42
2.1.3. C-H OXIDATION OF METHYL AROMATICS TO AROMATIC ESTER 44
2.1.4. C-H OXIDATION OF METHYL AROMATICS TO AMIDE OR NITRILE 45
2.2. MOTIVE 48
2.3. RESULT AND DISCUSSION 49
2.3.1. BENZYLIC C-H OXIDATION OF 4-METHYLANISOLE IN PIFA SYSTEM 49
2.3.2. BENZYLIC C-H OXIDATION OF 4-METHYLANISOLE IN PIDA SYSTEM 50
2.3.3. BENZYLIC C-H OXIDATION OF 4-METHYLANISOLE IN PIDA AND TFA SYSTEM 51
2.3.4. BENZYLIC C-H OXIDATION OF 4-METHYLANISOLE IN PIDA/TFA/ACOH SYSTEM 52
2.3.5. BENZYLIC C-H OXIDATION OF METHYL AROMATICS IN PIDA/TFA /ACOH SYSTEM 54
2.3.6. ESI(+)-MS SPECTRA FOR ANALYSIS OF PIDA/TFA/ACOH INTHF 56
2.3.7. POSTULATED MECHANISM FOR BENZYLIC C-H OXIDATION BY PIDA/ TFA/ACOH SYSTEM 58
2.3.8. SOLVENT EFFECT 63
2.3.9. TREATMENT OF P-METHYLANISOLE WITH IODOSYLBENZENE 64
2.3.10. DEPROTECTING GROUP USING PIDA/TFA/ACOH SYSTEM 65
2.3.11. ADD ACETATE ANHYDRATE TO INHIBIT THE C-H OXIDATION AT BENZYLIC POSTION 65
2.4. CONCLUSION 67
2.5. EXPERIMENT 68
2.5.1. GENERAL 68
2.5.2. COMPOUND DATA 68
2.6. REFERENCES 71
PART II-CHEMISTRY AND BIOLOGY OF TRIAZOLE-PYRROLE: CLICK CHEMISTRY AND DNA INTERACTION 73
1. INTRODUCTION 73
1.1. COPPER(I)-CATALYZED REGIOSELECTIVE FOR TRIAZOLE-FORMATION 74
1.2. DUPLEX DNA 76
1.3. TRIAZOLES : DNA MINOR GROOVE BINDING REAGENT 81
1.4. HYBRID TWO DIFFERENT DNA LIGANDS BY CLICK REACTION 86
1.5. TRIAZOLE COMPOUNDS FOR STABILIZE G-QUADRUPLEX 90
1.6. TRIAZOLE PHOTONUCLEASES 97
2. MOTIVE 105
3. RESULT AND DISCUSSION 107
3.1. SYNTHESIS OF TRIAZOLE-TRIPYRROLE COMPOUND 107
3.2. BINDING STUDIES 110
3.2.1. UV DNA MELTING TEMPERATURE (ΔTM) MEASUREMENT 110
3.2.2. ETHIDIUM BROMIDE DISPLACEMENT ASSAY 111
3.2.3. DNASE I FOOTPRINTING STUDIES 112
4. EXPERIMENTAL 116
4.1. GENERAL 116
4.2. DNA MELTING TEMPERATURE (TM) MEASUREMENT 116
4.3. ETHIDIUM BROMIDE DISPLACEMENT ASSAY 117
4.4. DNASE I FOOTPRINTING STUDIES 117
4.5. SYNTHESIS 118
5. CONCLUSION 129
6. REFERENCES 130

Part 1
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Part 2
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