The Chemistry of Benzotriazole Derivatives: A Tribute to Alan Roy Katritzky PDF
Preview The Chemistry of Benzotriazole Derivatives: A Tribute to Alan Roy Katritzky
Topics in Heterocyclic Chemistry 43 Series Editors: Bert Maes · Janine Cossy · Slovenko Polanc Jean-Christophe M. Monbaliu Editor The Chemistry of Benzotriazole Derivatives A Tribute to Alan Roy Katritzky 43 Topics in Heterocyclic Chemistry SeriesEditors: Bert Maes, Antwerp, Belgium Janine Cossy, Paris, France Slovenko Polanc, Ljubljana, Slovenia Editorial Board: D. Enders, Aachen, Germany S.V. Ley, Cambridge, UK G. Mehta, Bangalore, India R. Noyori, Hirosawa, Japan L.E. Overmann, Irvine, CA, USA A. Padwa, Atlanta, GA, USA Aims and Scope The series Topics in Heterocyclic Chemistry presents critical reviews on present andfuturetrendsintheresearchofheterocycliccompounds.Overallthescopeisto covertopicsdealingwithallareaswithinheterocyclicchemistry,bothexperimental andtheoretical,ofinteresttothegeneralheterocyclicchemistrycommunity. The series consists of topic related volumes edited by renowned editors with contributionsofexpertsinthefield. Moreinformationaboutthisseriesathttp://www.springer.com/series/7081 Jean-Christophe M. Monbaliu Editor The Chemistry of Benzotriazole Derivatives A Tribute to Alan Roy Katritzky With contributions by (cid:1) (cid:1) (cid:1) (cid:1) T. Albers K. Bajaj J.K. Beagle O.I. Bolshakov A.F. Gameiro (cid:1) R. Ge´rardy (cid:1) D.N. Haase (cid:1) I.O. Lebedyeva (cid:1) (cid:1) (cid:1) (cid:1) J.-C.M. Monbaliu M.V. Povstyanoy V. Povstyanoy (cid:1) R. Sakhuja D.L. Watkins Editor Jean-ChristopheM.Monbaliu CenterforIntegratedTechnologyandOrganicSynthesis–CiTOS DepartmentofChemistry UniversityofLie`ge Lie`ge Belgium ISSN1861-9282 ISSN1861-9290 (electronic) TopicsinHeterocyclicChemistry ISBN978-3-319-31552-2 ISBN978-3-319-31554-6 (eBook) DOI10.1007/978-3-319-31554-6 LibraryofCongressControlNumber:2016938784 #SpringerInternationalPublishingSwitzerland2016 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilarmethodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthis book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained hereinorforanyerrorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper ThisSpringerimprintispublishedbySpringerNature TheregisteredcompanyisSpringerInternationalPublishingAGSwitzerland Dedicated to Alan Roy Katritzky . Preface Eachchapterwithinthisvolumecriticallysurveystheapplicationsofbenzotriazole derivativesinavarietyofimportantsyntheticapplicationsrangingfromheterocy- clic chemistry to peptide constructs. The most significant developments and concepts in benzotriazole methodology are presented using selected examples. Eachchapterisdesignedtoprovidethenon-specialistreaderwithalltheimportant concepts and methodology that led to the development of a general benzotriazole methodology. Beyond the concepts and important developments, these contributions also offer an outlook on potential future developments in benzotriazolechemistry. Chapter“Preparation,Reactivity,andSyntheticUtilityofSimpleBenzotriazole Derivatives”introducesthereaderwiththespecificreactivityofbenzotriazoleand its simple derivatives. The preparation, synthetic properties and applications of a representative set of important and versatile benzotriazole derivatives are illustrated. Chapter “Acylbenzotriazoles: New Allies for Short Linear and Cyclic PeptideConstructs”gathersthemostimportantadvancesinthepreparationanduse of acylbenzotriazole derivatives for the preparation of oligopeptide constructs. Chapter “Benzotriazole-Based Strategies Towards Peptidomimetics, Conjugates and Other Peptide Derivatives” extends the discussion on the versatility of acylbenzotriazole derivatives towards the preparation of peptidomimetics, conjugates and other peptide derivatives. Chapter “Benzotriazole-Mediated Syn- thesis of Oxygen Containing Heterocycles” discusses benzotriazole-mediated strategies towards oxygen-containing heterocycles, and Chapter “Benzotriazole- Mediated Synthesis of Nitrogen Containing Heterocycles” reviews benzotriazole- mediated strategies towards nitrogen-containing heterocycles. Last but not least, Chapter“Benzotriazole:MuchMoreThanJustSyntheticHeterocyclicChemistry” regroups various applications of benzotriazole and its derivatives to medicinal chemistryandmaterialssciences. vii viii Preface Dedication Every domain in society has its own icons who are well known for their contributions and their leadership in the field. Certainly in sports, the role of iconsisenormousandstimulatesmanyyoungsterstoengageincertainsports. Also,scienceshavetheiricons. Whentalkingaboutheterocyclicsynthesis,Ibelievethatnoonewilldoubtthat AlanKatritzkyisandhasbeenaniconduringhiscareerandwillstayoneforalong time.TogetherwithhisgoodfriendCharlesRees,theyhadatremendousimpacton the field and studied heterocycles in a very systematic way. The numerous books thatAlaneditedonheterocyclicchemistryorganisedthefieldindifferentclassesof heterocycles.Alanstudiedextensivelytheirspecificreactivity,theirconformational behaviour,theirphysicochemicalpropertiesandtheiraromaticityandheterocyclic rearrangements. Picture:AlanR.KatritzkyreceivesthehonorarydoctorateatGhentUniversityin2001. AlanKatritzky(bornAugust18,1928)wasraisedandeducatedinEnglandand prepared his first heterocyclic compound at the age of 15. From 1948 to 1958, he spent time at Oxford, obtaining his degree in 1952 and publishing his first benzotriazolepaperin1953.HeperformeddoctoralworkwithSirRobertRobinson andreceivedaPhDin2years.In1957,AlanmovedtoCambridgeandbecamethe founding fellow of Churchill College, of which Sir John Cockcroft, Nobel Prize winner in1951 forhisworkonatom splitting, wasthefirst master. In1962,Alan Preface ix Katritzky moved to the new University of East Anglia in Norwich as founding professor of chemistry where he met Sir Christopher Ingold, member of the AcademicPlanningBoard.Quickly,hebecamedeanofthefacultyinEastAnglia andsucceededinconvincingtheauthoritiestoconstructanewchemistrybuilding which was opened by her Majesty the Queen. In 1980, Prof. Katritzky moved to FloridaasKenanprofessorofchemistrywherehehasbeenrunningsincethenabig international groupofpostdocsandPhDsstudyingseveralaspectsofheterocyclic chemistry. Alan passed away on February 10, 2014, in Gainesville after a fully filledlifeofchemistry. The contributions of Alan Katritzky tothe international scientific literature are elaborate with over 2500 international peer-reviewed papers and numerous book series(AdvancesinHeterocyclicChemistry,ComprehensiveHeterocyclicChemis- try, etc.). His scientific drive was exceptional. Up to the last moments, Alan was takinginitiativesandleadingabigmulticulturalresearchgroup.Hisknowledgeand drive have led to the creation of the Center for Heterocyclic Compounds at the DepartmentofChemistryinGainesville,Florida,witharesearchgroupofaround 50postdocsandPhDsworkingonheterocyclicchemistryovertheyears.Organised as ever, he was able to get the best out of his co-workers and built an impressive networkcoveringallcontinents.Hisworkwasalsointernationallyrecognisedwith morethantenhonorarydoctoratetitlesandnumerousprestigiousawards.Hisgood friendProf.AlPadwacategorisedAlanasasuperachiever. Alan Katritzky also spread the word. He travelled all over the globe and presented his views with a clear voice. As we all remember, Alan did not need a microphoneevenlecturinginfrontofhundredsofchemists.Healsolovedtolecture in other languages since he was eager to learn foreign languages. Not only in academic circles was Alan well known, he was also very well recognised in the chemicalindustryandhasbeenconsultingforallmajorchemicalandpharmaceuti- calcompaniesintheUSAandEurope. Alan Katritzky was also a person with a great humanitarian spirit. He founded Arkivoc,anelectronicscientificjournal,inordertogiveopportunitiestodevelop- ing countries to publish their work for free and also download all other Arkivoc articles for free. He strongly believed that scientific information is key to human andsocialdevelopmentandthereforehecreatedArkivoc.Arkivocisfunctioningon a personal donation of Alan and his wife Linde, is supported by the FLOHET conferenceinGainesville(Florida,USA)andisrunthroughtheeffortsofateamof scientistswhoperformalltheeditorialworkforfree.Arkivocwasveryclosetohis heartsincehewantedreallytohelpchangetheworldforthebetter.Hewantedto getthingsdoneand“bochra”(tomorrow)wasnothighonthelistofhisvocabulary. He was a charismatic mentor of his team of collaborators. With an amazing workingpowerandwithfirmleadership,diplomacyandBritishhumour,hepaved thewayforatremendousscientificcareerandhelpedmanycollaboratorsthrough- outtheircareers.Membersandex-groupmemberswerealwayswarmlywelcomed byLindeandAlan.Manyofushaveenjoyedthedinnersandtheselectedexcellent wines“atProf’splace”.
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