Nitropyridyl isocyanates in 1,3‐dipolar cycloaddition reactions

Holt, Jarle; Fiksdahl, Anne

doi:10.1002/jhet.5570440215

Cited by 22 publications

(10 citation statements)

References 29 publications

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“…An interesting example is cycloaddition of pyridine N-oxides with 2-and 4-pyridyl isocyanates derivatives, generated in situ by a Curtius rearrangement of the corresponding acyl azides, that in turn had been prepared form carboxylic acids upon treatment with diphenylphosphoryl azide (Scheme 24) [103,104]. These reactions, performed in dry boiling benzene, yield bis(pyridyl)amines in 65-80% yield.…”

Section: Cycloaddition To Carbon-nitrogen Multiple Bondsmentioning

confidence: 98%

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Loska

2017

Topics in Heterocyclic Chemistry

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1,3-Dipolar cycloaddition of N-oxides of azines and azoles has become a reliable and versatile synthetic method of preparation of highly functionalized nitrogen heterocycles. Mechanisms of cycloaddition of N-oxides are outlined, including various reaction pathways available for the initial five-membered cycloadducts. Cycloaddition to multiple carbon-carbon, carbon-nitrogen, and carbon-sulfur bonds is discussed, with particular emphasis on modern methods of selective C-2-functionalization of the heteroaromatic ring.

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Section: Cycloaddition To Carbon-nitrogen Multiple Bondsmentioning

confidence: 98%

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Loska

2017

Topics in Heterocyclic Chemistry

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“…[41a, 92,306,[408][409][410][411][412][413][414][415] In this context it would, of course, be inexcusable not to mention K. B. Sharpless' work (and that of his predecessors) on inter-and intramolecular cycloadditions of organic azides and NaN 3 to "nitriles attached to heteroatoms (O, S, N)", i.e., cyanates, thiocyanates and cyanamides (cf. in particular Introduction and chapter 1).…”

Section: Isothiocyanate Addition Productsmentioning

confidence: 99%

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Fehlhammer

Beck

2015

Zeitschrift anorg allge chemie

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Abstract. In whatever state of bonding -whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal -the azide moiety N 3 is characterized by its high potential of reactivity which essentially manifests itself in two basic processes: the elimination of dinitrogen and the entry into 1,3-dipolar cycloadditions with suitable dipolarophiles, the latter of which clearly predominates the chemistry of azide, also that of its metal compounds. In a preceding review entitled "Part I -Metal Azides: Overview, General Trends and Recent Developments" which was meant to lay the foundations for the present paper, these and other reactions have already been touched upon. The present review -Part II -now focusses in great detail on the formation of five-membered heterocyclestetrazol(at)es, triazol(at)es, triazolin(at)es, thiatriazol(at)es, etc. as well as various consecutive products -from azide and nitriles, isocyanides, alkynes, alkenes and heteroallenes (CS 2 , RN=C=S) in the ligand sphere of the metal. Generally, these [3+2]-cycloadditions are found to CONTENTS

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“…The reaction of heterocyclic N ‐oxides with isocyanates [ 45–47 ] usually proceeds under mild conditions through the initial [3+2]‐dipolar cycloaddition. The initially formed cycloadduct eliminates CO 2 , resulting in amino derivatives.…”

Section: Deoxygenative C–h Functionalizationmentioning

confidence: 99%

“…The reaction of heterocyclic N-oxides with isocyanates [45][46][47] As a rule, isocyanates are generated in situ from acyl azides as a result of the thermal Curtius rearrangement. Synthetic protocols developed to date allow amination of a wide range of azine N-oxides, including modification of molecules of importance in biomedical research (Scheme 25).…”

Section: Deoxygenative Aminationmentioning

confidence: 99%