- 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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- Decarboxylative hydrazination of unactivated carboxylic acids by cerium photocatalysis
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We report the cerium photocatalyzed radical decarboxylative hydrazination of carboxylic acids with di-tert-butylazodicarboxylate (DBAD). The operationally simple protocol provides rapid access to synthetically useful hydrazine derivatives and overcomes current scope limitations in the photoredox-catalyzed decarboxylation of carboxylic acids.
- Yatham, Veera Reddy,Bellotti, Peter,K?nig, Burkhard
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supporting information
p. 3489 - 3492
(2019/03/26)
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- Simple preparation of monoalkylhydrazines
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Alkylation of t-butyl isopropylidene carbazate with alkyl bromides occurs under phase-transfer conditions. Acid hydrolysis of the product completes a simple two-step synthesis of monoalkylhydrazines.
- Meyer, Kevin G.
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p. 2355 - 2356
(2007/10/03)
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- Synthesis of N-propargylphenelzine and analogues as neuroprotective agents
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A series of N1- and N2-propargylphenelzine derivatives and analogues (1-7) was synthesized. In addition to their activity as monoamine oxidase inhibitors, two of the compounds, N1- and N2-propargylphenelzines (3 and 6), were found to be potent at preventing DSP-4-induced noradrenaline (NA) depletion in mouse hippocampus, suggesting that they have neuroprotective properties.
- Ling, Lei,Urichuk, Liana J.,Sloley,Coutts, Ronald T.,Baker, Glen B.,Shan, Jacqueline J.,Pang, Peter K.T.
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p. 2715 - 2717
(2007/10/03)
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- N-tert-butoxycarbonylaminophthalimide, a versatile reagent for the conversion of alcohols into alkylated tert-butylcarbazates or hydrazines via the Mitsunobu protocol
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An efficient two-step method has been developed for the conversion of alcohols to substituted hydrazines. The use of N-tert- butoxycarbonylaminophthalimide as an acid partner in Mitsunobu reactions with a variety of alcohols permits the synthesis of the corresponding monoalkylated tert-butylcarbazates and hydrazines.
- Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Grégoire, Brigitte
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p. 205 - 207
(2007/10/03)
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