Heterocyclic Chemistry in the 21st Century A Tribute to Alan Katritzky

328 Pages·2016·18.03 MB·English

by  Eric F.V. Scriven and Christopher A. Ramsden (Eds.)

VOLUMEONEHUNDREDANDNINETEEN
A
DVANCES IN
HETEROCYCLIC CHEMISTRY
Heterocyclic Chemistry in the
21st Century: A Tribute to
Alan Katritzky
EDITORIAL ADVISORY BOARD
A. T. Balaban Galveston, Texas, United States of America
A. J. Boulton Norwich, United Kingdom
M. Brimble Auckland, New Zealand
D. L. Comins Raleigh, North Carolina, United States of America
J. Cossy Paris, France
J. A. Joule Manchester, United Kingdom
V. I. Minkin Rostov-on-Don, Russia
B. U. W. Maes Antwerp, Belgium
A. Padwa Atlanta, Georgia, United States of America
V. Snieckus Kingston, Ontario, Canada
B. Stanovnik Ljubljana, Slovenia
C. V. Stevens Ghent, Belgium
J. A. Zoltewicz Gainesville, Florida, United States of America
VOLUME ONEHUNDREDAND NINETEEN
A
DVANCES IN
HETEROCYCLIC CHEMISTRY
Heterocyclic Chemistry in the
21st Century: A Tribute to
Alan Katritzky
Editors
ERIC F. V. SCRIVEN
Department of Chemistry,
University of Florida,
Gainesville, FL, USA
CHRISTOPHER A. RAMSDEN
Lennard-Jones Laboratories,
Keele University, Staffordshire,
United Kingdom
AMSTERDAM(cid:129)BOSTON(cid:129)HEIDELBERG(cid:129)LONDON
NEWYORK(cid:129)OXFORD(cid:129)PARIS(cid:129)SANDIEGO
SANFRANCISCO(cid:129)SINGAPORE(cid:129)SYDNEY(cid:129)TOKYO
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CONTRIBUTORS
ScottBur
DepartmentofChemistry,GustavusAdolphusCollege,St.Peter,MN,USA
ChristosP.Constantinides
DepartmentofChemistry,NorthCarolinaStateUniversity,Raleigh,NC,USA
JanineCossy
LaboratoiredeChimieOrganique,InstituteofChemistry,BiologyandInnovation(CBI),
UMR8231,ESPCIParis/CNRS/PSL*ResearchUniversity,Paris,France
AmandineGuérinot
LaboratoiredeChimieOrganique,InstituteofChemistry,BiologyandInnovation(CBI),
UMR8231,ESPCIParis/CNRS/PSL*ResearchUniversity,Paris,France
C.DennisHall
DepartmentofChemistry,UniversityofFlorida,Gainesville,FL,USA
JohnA.Joule
TheSchoolofChemistry,TheUniversityofManchester,Manchester,UK
PanayiotisA.Koutentis
DepartmentofChemistry,UniversityofCyprus,Nicosia,Cyprus
MatthiasM.A.Moens
SynBioCResearchGroup,DepartmentofSustainableOrganicChemistryandTechnology,
FacultyofBioscienceEngineering,GhentUniversity,Ghent,Belgium
MarineMovsisyan
SynBioCResearchGroup,DepartmentofSustainableOrganicChemistryandTechnology,
FacultyofBioscienceEngineering,GhentUniversity,Ghent,Belgium
ChristianF.Otto
ClausthalUniversityofTechnology,Clausthal-Zellerfeld,Germany
AlbertPadwa
DepartmentofChemistry,EmoryUniversity,Atlanta,GA,USA
SivaS.Panda
DepartmentofChemistryandPhysics,AugustaUniversity,Augusta,GA,USA
AndreasSchmidt
ClausthalUniversityofTechnology,Clausthal-Zellerfeld,Germany
BrankoStanovnik
FacultyofChemistryandChemicalTechnology,UniversityofLjubljana,Ljubljana,Slovenia
ChristianV.Stevens
SynBioCResearchGroup,DepartmentofSustainableOrganicChemistryandTechnology,
FacultyofBioscienceEngineering,GhentUniversity,Ghent,Belgium
j
ix
x Contributors
SaschaWiechmann
ClausthalUniversityofTechnology,Clausthal-Zellerfeld,Germany
ViktorV.Zhdankin
DepartmentofChemistryandBiochemistry,UniversityofMinnesotaDuluth,Duluth,
MN,USA
PREFACE
A short tribute to Alan Katritzky, highlighting aspects of his major work in
heterocyclic chemistry (structure, mechanism, theory, QSAR, synthetic
methods, applications, and the review literature) appeared in Volume 113
ofAdvancesinHeterocyclicChemistry.Forover50years,Alanwasatthefore-
frontofadvancesinandapplicationsofheterocyclicchemistry.Heinitiated
the publication of Advances in Heterocyclic Chemistry in 1963 and personally
commissioned and edited 112 volumes. When we considered what would
be a fitting tribute to his contribution, we posed the question, as we felt
Alan would have, “What is happening now, and what next?” In response
tothisquestion,wehavebeenfortunatetoreceive27chaptersfromleaders
currently involved in heterocyclic chemistry and its applications. These
chapters cover the latest advances in the areas mentioned above together
with a broad scope of new developments.
Thefirstvolumeofthisthree-volumetributecontainsninechapters.In
Chapter 1, Dennis Hall (University of Florida) and Siva Panda (Augusta
University) highlight the important contribution of Alan Katritzky’s
workonsynthetic application of 1H-benzotriazole as ahalogen surrogate.
In Chapter 2, Marine Movsisyan, Matthias Moens, and Christian Stevens
(Ghent University) describe the use of microreactors and illustrate their
applications and advantages using selected examples of the flow synthesis
of heterocycles. The structure and synthetic applications of hypervalent
heterocyclic derivatives of nonmetal main-group elements (B, Si, P, S,
Se,Br,andI)arethesubjectofChapter3byViktorZhdankin(University
of Minnesota Duluth). The next two chapters cover new aspects of
heterocyclic natural products. In Chapter 4, John Joule (The University
of Manchester) highlights novel aspects of natural products containing
nitrogen heterocycles that have been revealed in the period 1990–2015.
Chapter 5 by Janine Cossy and Amandine Guérinot (ESPCI Paris/
CNRS/PSL* Research University) describes advances during the period
1990–2015 in the synthesis of natural products containing oxygen
heterocycles.
The generationof three-to eight-memberedN-heterocyclic carbenes is
reviewed by Andreas Schmidt, Sascha Wiechmann and Christian F. Otto
(ClausthalUniversityofTechnology)inChapter6.ChristosConstantinides
(North Carolina State University) and Panayiotis A. Koutentis (University
of Cyprus) review recent developments in the synthesis and applications
j
xi
xii Preface
ofstableN-andN/S-richheterocyclicradicalsinChapter7.Newdevelop-
mentsinheterocyclictautomerismwithparticularreferencetodesmotropes,
carbenes, and betaines are reviewed in Chapter 8 by Branko Stanovnik
(University of Ljubljana). The volume concludes with a review by Albert
Padwa (Emory University) and Scott Bur (Gustavus Adolphus College) of
recentadvancesintheuseof1,3-dipolarcycloadditionsinalkaloidsynthesis.
Chris Ramsden and Eric Scriven
April, 2016
CHAPTERONE
The Benzotriazole Story
C. Dennis Hall1,*, Siva S. Panda2
1DepartmentofChemistry,UniversityofFlorida,Gainesville,FL,USA
2DepartmentofChemistryandPhysics,AugustaUniversity,Augusta,GA,USA
*Correspondingauthor:E-mail:[email protected]
Contents
1. 1H-BenzotriazoleasaSyntheticTool 3
2. 1H-BenzotriazoleintheSynthesisofHeterocycles 5
3. Acylation,Aroylation,andHeteroaroylationbyBtTechnology 7
4. Alkylations,Heteroalkylations,andBt-StabilizedCarbanions 9
4.1 AlkylationsandHeteroalkylations 9
4.2 Bt-StabilizedCarbanions 10
5. RearrangementsofBenzotriazoleDerivatives 10
6. BenzotriazoleintheSynthesisofPeptidesandIsopeptides 11
7. BenzotriazoleintheSynthesisofAminoAcid/PeptideBioconjugates 12
8. NativeChemicalLigationUsingBenzotriazoleChemistry 16
9. BenzotriazoleintheSynthesisofCyclicPeptidesandCyclicPeptidomimetics 18
10. BenzotriazoleintheSynthesisofPeptidomimetics 20
11. Conclusion 20
References 20
Abstract
Theutilityof1H-benzotriazoleasahalogensurrogateinacylation,aroylation,andalkyl-
ationreactionsisreviewedtogetherwithitsapplicationtothesynthesisofheterocycles,
peptides,isopeptides,cyclicpeptides,peptidomimetics,andpeptideconjugates.
Keywords:
Amino acids; Benzotriazole; Conjugates; Halogen surrogate; Heterocycles;
Peptides;Synthesis
When Alan Katritzky died on February 10, 2014, over 2170 research papers
alone were credited to his name, 636 of which dealt with various aspects
ofbenzotriazole (Bt)chemistry.Sincehisdeath,another 40þpapersincor-
porating someaspects of Bt technology have appeared or are due to appear
in the literature. This review therefore seeks to do justice to 25years of
intensiveresearchbyfocusingonthehighlightsofARK’sBtcontributions.
AdvancesinHeterocyclicChemistry,Volume119
ISSN0065-2725 ©2016ElsevierInc. j
1
http://dx.doi.org/10.1016/bs.aihch.2016.01.001 Allrightsreserved.
2 C.DennisHallandSivaS.Panda
ThisaspectofAlan’sworkbeganin1990andtothisdaythereisanotice
pinned to the wall of the Katritzky Conference Room at the University of
Floridawhich urgesus torememberthat “3months ofworkin thelabora-
torycansaveyou3hinthelibrary”(orinmodernparlance,savesometime
on the Internet). True to form, Alan began the benzotriazole phase of his
work by a review entitled, “Benzotriazole, a novel synthetic auxiliary”
(1991T2683). Subsequent years saw reviews appearing on further aspects
of benzotriazole as a synthetic tool (1998CRV409) (1999JHC1501,
2003CEJ4586), on the use of benzotriazole in heterocyclic synthesis (1996
T15031, 1998JHC1123, 2010CRV1564, 2011CRV7063), N-acylbenzo-
triazoles (2005SL1656), Bt-mediated alkylation (2005T2555), Bt-stabilized
carbanions (1994AA31), heterocyclic rearrangements (1993H483), bio-
conjugates (2009ARK248), and finally the synthesis of peptides (2009
SL2392)andpeptideconjugates(2013AA43).Thelasttwotopicsrepresent
the culmination and zenith of a sustained effort in a rich field which gave
Alan a great deal of satisfaction.
Sowhatisitthatgivesbenzotriazolesuchubiquitousutility?Toanswer
thatrhetoricalquestionwemustfirstlookatthestructureandpropertiesof
benzotriazole(1ab)itself(Scheme1).Thequinonoidform(1b)islessstable
than the benzenoid tautomer (by ca. 9.5kcal/mol) so most derivatives of
Bt appear as the (N)-1 isomer although the proportion of (N)-2 isomer
increases with the steric bulk of the N-substituents (1990JOC5683,
1990JCS(P2)2059).
The molecule is a weak acid (pKa 8.2) but is also a very weak base
(pKa<0) and consequently is soluble in aqueous sodium carbonate or
1MHCl,thusaffordingtwopotentialmethodsofseparationfromreaction
mixtures. Themolecule is both electron attracting,thusstabilizingcarban-
ions, and electron donating giving rise to acyl, aroyl, phosphonyl, and
sulfonylderivativesofsyntheticutility(videinfra).Mostimportantly,how-
ever,benzotriazolebehavesasaleavinggroupsurrogateforhalogenandin
thisrespectaffordsthedistinctadvantagesofbenzotriazolederivativesbeing
(1) easy to prepare, (2) stable to air and moisture over long periods of time
but, (3) sufficiently reactive to duplicate most reactions of their halogen
analogs.
Scheme1