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The Chemistry of Homophthalic Acid

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The Chemistry of Homophthalic Acid DEVELOPMENT OF NEW SYNTHETIC METHODOLOGIES FOR THE SYNTHESIS OF UNUSUAL ISOCOUMARIN AND INDOLE DERIVATIVES: THE CHEMISTRY OF HOMOPHTHALIC ACID A THESIS SUBMITTED TO THE GRADUATE SCHOOL OF NATURAL AND APPLIED SCIENCES OF MIDDLE EAST TECHNICAL UNIVERSITY BY SEVİL ÖZCAN IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGRE OF DOCTOR OF PHILOSOPHY IN DEPARTMENT OF CHEMISTRY JANUARY 2007 Approval of the Graduate School of Natural and Applied Sciences Prof. Dr. Canan Özgen Director I certify that this thesis satisfies all the requirements as a thesis for the degree of Doctor of Philosophy. Prof. Dr. Ahmet Önal Head of Department This is to certify that we have read this thesis and that in our opinion it is fully adequate, in scope and quality, as a thesis for the degree of Doctor of Philosophy. Prof. Dr. Metin Balcı Supervisor Examining Committee Members Prof. Dr. Canan Ünaleroğlu (Hacettepe UNV, CHEM) Prof. Dr. Metin Balcı(METU, CHEM) Prof. Dr. Basri Atasoy (GAZİ UNV., CHEM EDUC.) Prof. Dr. Bekir Peynircioğlu (METU, CHEM) Prof. Dr. Metin Zora (METU, CHEM.) I hereby declare that all information in this document has been obtained and presented in accordance with academic rules and ethical conduct. I also declare that, as required by these rules and conduct, I have fully cited and referenced all material and results that are not original to this work. Name, Last Name: SEVİL ÖZCAN Signature : iii ABSTRACT DEVELOPMENT OF NEW SYNTHETIC METHODOLOGIES FOR THE SYNTHESIS OF UNUSUAL ISOCOUMARIN AND INDOLE DERIVATIVES: THE CHEMISTRY OF HOMOPHTHALIC ACID ÖZCAN, Sevil Ph. D., Department of Chemistry Supervisor: Prof. Dr. Metin Balcı January 2007, 401 pages. Many heterocyclic compounds containing nitrogen, oxygen and sulfur show wide range of physiological activities and their synthesis has always been attracted the interest of chemists. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of isocoumarines, indoles, isoquinolines, benzodiazepinones and quinazolines, which have been found to show important biological activities. Starting from homophthalic acid and bishomophthalic acid the corresponding acyl azides were proposed to be synthesized, which then would be used for the synthesis of various heterocycles. The proposed diazide from homophthalic was not formed due to the tendency of the ortho-positioned acid to undergo cyclization. iv Instead, new unusual benzochromen and isocoumarin derivatives have been synthesized in a single step, for which reasonable mechanisms have been proposed. The half ester produced from homophthalic acid was an important key compound for the synthesis of new highly substituted indole derivatives, which are expected to be biologically active. The diisocyanate derived from was synthesized directly from ortho-bromo xylene was treated with alcohols and hydrazine to produce seven membered rings. Instead of the intramolecular cyclization reaction, they underwent polymerization to form new polymers. Furthermore, new synthetic method for the synthesis of pyrazoles has been developed. Key words: isocoumarin, isoquinoline, indole, benzodiazepinone, quinazoline, polyurethane, pyrazole. v ÖZ İLGİNÇ İZOKUMARİN VE İNDOL TÜREVLERİNİN SENTEZİ İÇİN YENİ SENTETİK METODLARIN GELİŞTİRİLMESİ: HOMOFİTALİK ASİDİN KİMYASI ÖZCAN, Sevil Doktora, Kimya Bölümü Tez Yöneticisi: Prof. Dr. Metin Balcı Ocak 2007, 401 sayfa Nitrojen, oksijen ve sulfur içeren pek çok heterosiklik bileşik geniş ölçüde fizyolojik aktivite gösterirler ve sentezleri her zaman kimyacıların ilgisini çekmiştir. Bu tezin amacı önemli biyolojik aktiviteler göstermesi beklenen yeni izokumarin, indol, izokinolin, benzodiazepinon ve kinazolin türevlerinin sentezlerini hedefleyen yeni sentetik metotlar geliştirmektir. Çeşitli heterosikliklerin sentezinde kullanılmak üzere homofitalik ve bishomofitalik asitten çıkarak ilgili açil azidlerin sentezlenmesi tasarlanmıştır. Homofitalik asitten çıkılarak sentezi planlanan diazid, orto konumundaki asidin halka kapanması eğiliminden dolayı oluşmamıştır. Yapılan çeşitli azidinasyon reaksiyonlari ile yeni ilginç benzokromen ve izokumarin türevleri sentezlenip mekanizmaları tartışılmıştır. vi Homofitalik asitten sentezlenen yarı ester, biyolojik aktivite göstermesi beklenen poli sübstitüe indol türevlerin sentezinde önemli anahtar bileşik olmuştur. Orto bromo ksilenden sentezlenen diizosiyanat yedili halka oluşturmak üzere alkol ve hidrazinle muamele edilmiştir. Intramoleküler halkalaşma reaksiyonu yerine yeni polimerler oluşturmak üzere polimerleşme reaksiyonu gerçekleşmiştir. Ayrıca, pirazollerin sentezi için yeni bir sentetik metod geliştirilmiştir. Anahtar kelimeler: izokumarin, izokinolin, indol, benzodiazepinon, kinazolin, poli uretan, pirazol. vii To my parents, brother and little nephew CAN…. viii ACKNOWLEDGEMENTS I would like to present my great thanks to my supervisor Prof. Dr. Metin Balcı for his guidance, continuous interest, moral supports and encouragements. It was really a great opportunity for me to study under his supervision that I could learn a lot of things on the organic synthesis and NMR spectra interpretation. I feel very happy and lucky to be a student of Prof. Balcı. I deeply thank to NMR specialists Fatoş Polat Doğanel and Seda Karayılan for the NMR experiments. I would like to thank to Asst. Prof. Dr. Ertan Şahin for the X-ray diffraction analysis. I would like to express my special thanks to all the members of SYNTHOR® Research Group, especially to Dilem, Seda and Nihal for their friendships. We spent lots of nice times together which will have a special part in my memories. My special thanks also go to Benan. He was always an enjoyable and relaxing friend. I would also like to thank to my home mates Özlem, Mutlu, Nadide and Özge for their friendships, moral supports and for the enjoyable times that we had spent together. My great thanks go to the most important and special people in my life, my parents and brother for their endless love, moral support, interest and encouragement. ix TABLE OF CONTENTS PLAGIARISM.................................................................................................. iii ABSTRACT..................................................................................................... iv ÖZ..................................................................................................................... vi ACKNOWLEDGEMENTS.............................................................................. ix TABLE OF CONTENTS.................................................................................. x LIST OF FIGURES........................................................................................... xvi LIST OF ABBREVIATIONS........................................................................... xvii CHAPTER 1. INTRODUCTION........................................................................................ 1 1.1. Quinazolines........................................................................................... 1 1.1.1.The synthesis of Quinazolines ........................................................ 5 1.2. Isoquinolines.......................................................................................... 6 1.2.1. The synthesis of Isoquinolines......................................................... 10 1.3.Isocoumarines…..................................................................................... 13 1.3.1. The synthesis of Isocoumarines....................................................... 15 1.4. Indoles…..........................................................................…................. 24 1.4.1. The synthesis of Indoles………………………………………….. 29 1.4.2. Oxindoles…………………………………………………………. 35 1.5. Benzodiazepinones 42 1.5.1. The synthesis of 1,3-Benzodiazepinones…………………………. 43 1.5.2. The synthesis of 1,4-Benzodiazepinones…………………………. 45 1.5.3. The synthesis of 1,5-Benzodiazepinones…………………………. 51 1.5.4. The synthesis of 2,4-Benzodiazepinones…………………………. 53 1.6. The aim of the thesis………………………………………………….. 54 x 2. RESULTS AND DISCUSSION 55 2.1. The reaction of homophthalic acid with thionyl chloride: The 55 synthesis of homophthalic anhydride (298).................................................. 2.1.1. The reaction of homophthalic acid with N,N-dimethylchlorosulfite 57 methaniminium chloride in the presence of sodium azide: The synthesis of 6H-dibenzo[c,h]chromen-6-one (307).......................................................... 2.1.2. The reaction of homophthalic acid with N,N-dimethylchlorosulfite 63 methaniminium chloride in the absence of sodium azide: The synthesis of (4Z)-4-[(dimethylamino)methylene]-1H-isochromene-1,3(4H)-dione (327)………………………………………………………………………. 2.2. The reaction of homophthalic acid with triethyl amine and ethyl 66 chloroformate in the presence of sodium azide: The synthesis of unusual substituted isocoumarin derivatives (332), (333), (334) and (335)………... 2.2.1. Characterization of the compound (333)………………………….. 68 2.2.2. Characterization of the compound (332).......................................... 69 2.2.3. Synthesis and characterization of the compound (340)…………... 71 2.2.4. Characterization of the compound (334)....................................... 74 2.2.5. Characterization of the compound (335)........................................ 76 2.2.5.1 Acetylation of tetrahydroisoquinoline (345): Synthesis of 77 Quinazoline derivatives (346) and (347)............................................. 2.3. The reaction of homophthalic acid with triethyl
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