- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- N-Isocyanodialkylamines generated in situ for the Joullié–Ugi reaction with indolenines
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N-Isocyanodialkylamines are rare isocyanide surrogates for the Ugi-type reactions. To avoid problems with instability and the obnoxious smell of these reagents, we optimized and employed a convenient protocol for in situ dehydration of N,N-dialkyl-N′-formyl hydrazines to give the respective N-isocyanodialkylamines which were utilized in the reaction with indolenines and acetic acid. The reaction was demonstrated to give modest to excellent yields of products incorporating the N-isocyanodialkylamine but not the carboxylic acid component.
- Golubev, Pavel,Krasavin, Mikhail
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supporting information
p. 3532 - 3536
(2018/08/29)
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- Synthesis of substituted 1 H-indazoles from arynes and hydrazones
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The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.
- Li, Pan,Wu, Chunrui,Zhao, Jingjing,Rogness, Donald C.,Shi, Feng
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experimental part
p. 3149 - 3158
(2012/07/14)
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- A new type of anionic rearrangement in metalated benzylhydrazines
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Metalation of N,N-dibenzyl-N′-(trimethylsilyl)hydrazine with organyllithium and -magnesium compounds led to the migration of the benzyl group, and the deprotonation of Si-Me groups was observed. The syntheses and crystal structures of Bz12N-NH2, [Bz1(Li)N-N(SiMe3)Bz1]2, and [Mg-[Bz1N-N(SiMe2CH2])Bz1]2 are presented. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Sachdev, Hermann,Preis, Cordula
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p. 1495 - 1501
(2007/10/03)
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- N-NITRENES. II. INVESTIGATION OF THE MECHANISM OF DISSOCIATION OF DIBENZYLAMINONITRENE BY CHEMICALLY INDUCED POLARIZATION OF 1H NUCLEI. THE SPIN STATE OF DIBENZYLAMINONITRENE
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The mechanism of the dissociation of dibenzylaminonitrene and p-bromodibenzylaminonitrene into molecular nitrogen and hydrocarbon products was studied.Dibenzylaminonitrene forms dibenzyl and o- and p-benzyltoluenes.In the presence of thiophenol significant amounts of toluene are formed.During dissociation p-bromodibenzylaminonitrene gives a mixture of symmetrical and unsymmetrical dibenzyls.In the presence of octanethiol only unsymmetrical p-bromodibenzyl is formed.The dissociation of dibenzylaminonitrene takes place by synchronous cleavage of the two C-N bonds and the formation of a pair of benzyl radicals.Dibenzylaminonitrene dissociates from the singlet electronic state.
- Savin, V. I.
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- N-NITRENES. I. FORMATION OF FREE RADICALS IN THE DISSOCIATION OF DIBENZYLAMINONITRENE
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By ESR with spin traps it was shown that the dissociation of dibenzylaminonitrene to nitrogen and bibenzyl takes place through the formation of benzyl radicals.Various methods of generation of dibenzylaminonitrene in the presence of spin traps (2-methyl-2-nitrosopropane, nitrosodurene, phenyl-N-tert-butyl-nitrone) give spin adducts (nitroxyl radicals) stable at room temperature.The formation of two nitroxyl radicals during the dissociation of dibenzylaminonitrene labeled at one methylene group with deuterium imdicates that one molecule of dibenzylaminonitrene gives two benzyl radicals during dissociation.
- Savin, V. I.,Morozov, V. I.,Kitaev, Yu. P.
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p. 866 - 870
(2007/10/02)
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