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E-Book, Englisch, Band Volume 113, 338 Seiten

Reihe: Advances in Heterocyclic Chemistry

Advances in Heterocyclic Chemistry


1. Auflage 2014
ISBN: 978-0-12-800398-5
Verlag: Elsevier Science & Techn.
Format: EPUB
Kopierschutz: 6 - ePub Watermark

E-Book, Englisch, Band Volume 113, 338 Seiten

Reihe: Advances in Heterocyclic Chemistry

ISBN: 978-0-12-800398-5
Verlag: Elsevier Science & Techn.
Format: EPUB
Kopierschutz: 6 - ePub Watermark



Established in 1960, Advances in Heterocyclic Chemistry is the definitive serial in the area-one of great importance to organic chemists, polymer chemists and many biological scientists. Written by established authorities in the field, the comprehensive reviews combine descriptive chemistry and mechanistic insight and yield an understanding of how the chemistry drives the properties. - One of great importance to organic chemists, polymer chemists and many biological scientists - Written by established authorities in the field, the comprehensive reviews combine descriptive chemistry and mechanistic insight and yield an understanding of how the chemistry drives the properties

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Weitere Infos & Material


1;Front Cover;1
2;EDITORIAL ADVISORY BOARD;3
3;Advances in HETEROCYCLIC CHEMISTRY;4
4;Copyright;5
5;CONTENTS;6
6;CONTRIBUTORS;8
7;PREFACE;10
8;TRIBUTE FOR ALAN R. KATRITZKY;12
8.1;ALAN KATRITZKY 1928–2014;12
8.2;ALAN R. KATRITZKY—AN APPRECIATION OF HIS CONTRIBUTION TO THE CHEMICAL SCIENCES;15
8.3;REFERENCES;20
9;Chapter One - Dimethyl Acetylenedicarboxylate as A Building Block in Heterocyclic Synthesis†;22
9.1;1. INTRODUCTION;23
9.2;2. SYNTHESIS OF VARIOUS HETEROCYCLIC COMPOUNDS;24
9.3;3. SYNTHESIS OF FUSED HETEROCYCLIC COMPOUNDS;59
9.4;4. SYNTHESIS OF SPIRO-COMPOUNDS;74
9.5;5. SYNTHESIS OF MISCELLANEOUS HETEROCYCLES;78
9.6;6. CONCLUSIONS;81
9.7;ACKNOWLEDGMENTS;81
9.8;REFERENCES;81
10;Chapter Two - Chemistry of Pent-4-yne-1,3-diones (Acetylenic ß-diketones) as Precursors for Heterocyclic Compounds;88
10.1;1. INTRODUCTION;89
10.2;2. SYNTHESIS OF ACETYLENIC .-DIKETONES;90
10.3;3. REACTIONS OF ACETYLENIC .-DIKETONES;92
10.4;4. SPECTROSCOPIC PROPERTIES;127
10.5;ACKNOWLEDGMENTS;129
10.6;REFERENCES;129
11;Chapter Three - Aromaticity and Conjugation in 1,2-Benzoquinone Valence Isomers and Congeners;132
11.1;1. INTRODUCTION;133
11.2;2. DISCUSSION OF THE 10 KNOWN PAIRS OF VALENCE ISOMERS 1–10;137
11.3;3. RELATED STRUCTURES WITH OTHER HETEROATOMS;150
11.4;4. CONCLUDING REMARKS;155
11.5;REFERENCES;157
12;Chapter Four - Ketenes as Privileged Synthons
in the Syntheses of Heterocyclic
Compounds. Part 1: Three- and
Four-Membered Heterocycles†;164
12.1;1. INTRODUCTION;165
12.2;2. SYNTHESES OF VARIOUS HETEROCYCLIC COMPOUNDS;167
12.3;3. THREE-MEMBERED HETEROCYCLES WITH ONE HETEROATOM CONTAINING;167
12.4;4. FOUR-MEMBERED HETEROCYCLES WITH;169
12.5;5. CONCLUSION;249
12.6;ACKNOWLEDGMENTS;250
12.7;REFERENCES;250
13;Chapter 5 - Heterocycles from the Reaction of Thione Groups with Acetylenic Bonds;266
13.1;1. INTRODUCTION;267
13.2;2. FOUR-MEMBERED RING SYSTEMS;268
13.3;3. FIVE-MEMBERED RING SYSTEMS;269
13.4;4. SIX-MEMBERED RING SYSTEMS;298
13.5;5. SEVEN-MEMBERED RING SYSTEMS;317
13.6;6. EIGHT-MEMBERED RING SYSTEMS;318
13.7;7. CONCLUSION;319
13.8;ACKNOWLEDGMENTS;319
13.9;REFERENCES;319
14;INDEX;326


Tribute for Alan R. Katritzky
Alan Katritzky 1928–2014
For over 60 years, Professor Alan R. Katritzky was a pioneer in the development of the important field of heterocyclic chemistry. His truly monumental work has contributed much to the science that underpins the synthetic work of the modern pharmaceutical and agrichemical industries as well as that of dyestuffs and polymers. He systematically explored the gamut of basic heterocyclic chemistry to gain understanding. He employed large cohorts of graduate students and research fellows drawn from across the globe in an organization worthy of the military. His discoveries were reported in over 2300 papers published in the primary scientific literature. He was also a great educator. In 1961 he cowrote, with Jeanne M. Lagowski, the first modern textbook on heterocyclic chemistry (which was later translated into French, German, Italian, Japanese, Polish, Russian, and Spanish). He produced compilations and systematization of this chemistry in more than 200 books and, ahead of his time, he organized instructional courses attended by hundreds of industrial chemists. He was, as a consequence, in high demand as a consultant to many companies. This prolific career was spent at two universities: first, between 1962 and 1980, at the then newly founded University of East Anglia, Norwich, followed by the University of Florida, at Gainesville, USA. In the early 1960s, the University Grants Committee established seven new universities in the United Kingdom. Alan Roy Katritzky, was preappointed in 1962, at the age of 34, to be the Professor of Chemistry and the founding Head of a new School of Physical Sciences at the University of East Anglia. Said to be abrasively dynamic but with the firmest of ideas, he argued that the resources of a School were quite inadequate for the two multisubject disciplines as Chemistry and Physics and therefore he insisted, against the ideal of interdisciplinary Schools at first espoused by UEA, that he be appointed Head of a School of Chemical Sciences. This proposal immediately led to controversy with Arts colleagues, who assumed that Chemistry (or Physics) referred to a single subject; the two-word title was introduced to clarify this situation. With the support of two of the most powerful academic chemists in the United Kingdom, Lord Todd at Cambridge and Sir Robert Robinson at Oxford, his argument prevailed. Subsequently he recruited two more Professors, Norman Sheppard in Physical Chemistry from Cambridge and Stephen Mason in Chemical Spectroscopy from Exeter University. All three were in due course elected Fellows of the Royal Society. Within 5 years, the new School had recruited a complement of some 25 faculty members and, as well as an undergraduate teaching program, including the innovative subject of chemical education, had established a strong postgraduate research school with over 100 students. In 1980, he left Norwich for the endowed Kenan Chair of Chemistry at the University of Florida, Gainesville, USA. He had become only too aware that one day, at a time when he would still have much to offer, he would be required to retire if he remained in the United Kingdom. In Florida, his career entered a phase of even greater research intensity. For him it was a fresh start in a land of opportunity. There he founded the Center for Heterocyclic Compounds that facilitated postgraduate study and the translation of discoveries to industrial applications. Alan Katritzky came from a family of German-speaking immigrants living in the East End of London, from whom he acquired his powerful work ethic. His grandfather had migrated to England in 1871 from the village of Sypniewo (Zippnow) in Prussia (now Poland), lying halfway between Berlin and Danzig. His father, Charles, and mother, Emily Catherine (née Lane) Katritzky, were both born in London. Alan, born in Harringay on August 18, 1928, was one of four siblings, two sisters and two brothers. His father was a tailor, widely read, who was determined that all his children should have the best possible education. Indeed all went to Grammar School. Alan attended South Harringay Infant and Junior schools from 1933 but was evacuated in 1940 to Wisbech, Cambridgeshire, where he attended the High School. There his passion for chemistry was inspired by the chemistry master W.E. Fieldhouse. Alan prepared his first heterocyclic compound, the barbiturate drug Veronal, on his 15th birthday! Two years of compulsory National Service from 1946 provided him the opportunity for university study after demobilization. Encouraged by an Officer, he was able to secure a place at St Catherine's Society, Oxford in 1948. He also had the good fortune to meet his future wife, Linde Kilian, a lawyer's daughter from Munich, while on a skiing trip in 1949. They married in 1952. Alan read chemistry at Oxford, obtaining a first class honors degree followed by a doctorate (DPhil), in 1954, Alan's doctoral training was supervised by Professor Sir Robert Robinson. Alan thought himself fortunate to have had no fewer than five discussions with Sir Robert during the 2 years required to obtain the degree. Remarkably, he also found time to row for his college. His thesis was concerned with the structure of strychnine, and would have made a significant impact, but unfortunately it was found that Japanese workers had arrived at the same result in work that was published during the War, but which only came to light in the West several years later. He remained in Oxford as an independent researcher from 1954 to 1958 as Senior Demy at Magdalen College and college lecturer at Pembroke, directing a small but active research group. His interests at this time were mainly in the study of pyridine and its N-oxide, applying a wide variety of physicochemical techniques (infrared and ultraviolet spectra, dipole moment measurements) as well as studying and developing their chemical conversions. The Katritzkys left Oxford for Cambridge at the end of 1957. Alan liked to claim that Professor Sir Ewart Jones, FRS, Robinson's successor, was so extremely anxious to be rid of him that he wrote an unusually glowing letter of recommendation to Lord Todd. He first joined Trinity Hall, but later he became a Foundation Fellow of the then new Churchill College at Cambridge of which Sir John Cockcroft, FRS, was the first Master. Alan recollected that he was a person most skilled in imposing his will on a fractious body of Fellows in a seemingly mild manner. Such political maneuvering at Oxbridge colleges was, he later suggested, an excellent training that stood him in good stead at the University of East Anglia, particularly in the 1960s, a troublesome time for universities. During his career Alan Katritzky won academic distinction around the world, being awarded numerous honorary doctorates, professorships, and decorations, including election to the Royal Society of London. He maintained his prodigious level of output until a few days before his death at the age of 84 years. Alan Katritzky, an accomplished linguist in French, German, and Italian, undertook many lengthy lecture tours to Eastern Europe, the USSR, India, and China, establishing many useful contacts. These served to recruit the large number of students who subsequently joined his research group. With his wife, Linde, he funded a number of prizes and charitable foundations to support students. In 2000 the Katritzky family founded and financed a free online journal “Arkivoc” to provide researchers, especially those in the developing world, with the means to present their work in the primary literature free from publishing costs. Alan was forceful, direct and resolute in all his professional dealings, but always compassionate and warm in personal relationships. His lifetime commitment to, and achievement in, his chosen subject of chemistry was total. He died on February 10, 2014 after a fall. He is survived by his wife, Linde; his children Rupert, Margaret, Erika, and Freda; and three grandchildren Martin, Eric, and Elisabeth. Written by John Boulton and colleagues at UEA Alan R. Katritzky—An Appreciation of His Contribution to the Chemical Sciences
Alan Katritzky had a complete dedication to teaching and research in organic chemistry especially heterocyclic chemistry over a period of 60 years. Therefore, it is fitting to start this appreciation with mention of his first textbook, written with Jeanne Lagowski—Heterocyclic Chemistry which appeared in 1960—a thin book that contained a colossal amount of information, but many unanswered questions. Later followed Principles of Heterocyclic Chemistry (1967) again with Jeanne Lagowski; a textbook that went into many reprints and was translated into seven languages. Much of what we understand today of structure and reaction mechanisms in heterocyclic chemistry was not well understood even for the most common heterocycles in 1960. Alan studied the reactivity of heterocycles with great success using physical methods which were then newly available to organic chemists. He also tackled successfully the question of the structure of heterocycles that had bedeviled the efforts of many a good chemist before him. Reviews of this and subsequent research are cited that were written before and after his main contributions were published to give an appreciation of the impact of the work. A review of the chemistry of aromatic heterocyclic N-oxides that appeared in a 1956 article in Quarterly Reviews set the scene (56QR359). One of his first papers demonstrated that the N-oxide group could be either a source of electrons or an electron sink, depending on the electronic character of the substituent in the 4-position of the pyridine 1-oxide ring....



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