tert-Butyl derived and base labile protecting groups were completely stable under these conditions. This heterocycle may represent a type of privileged, By clicking accept or continuing to use the site, you agree to the terms outlined in our. In summary, magnesium/hydrazinium monoformate provides a convenient system for the selective reduction of aliphatic and aromatic nitro compounds. 0000009103 00000 n 0000009408 00000 n The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. Shankare Gowda. 0000011923 00000 n HTMo0>*Ze[PloPbmrlwiMCGJ(?R+,xTn[\E~4e( <4D#A| 'J*,d\`;]t SAn'ab=$d'3FBo_usSFI+OR0? Most of the reactions were completed within 2 min as monitored by the disappearance of the starting materials and concomitant formation of the product (TLC). HHS Vulnerability Disclosure, Help This Official DeepDyve plugin makes research easy by saving PubMed and GoogleScholar search results, and adding direct links to read articles at DeepDyve. sharing sensitive information, make sure youre on a federal The obtained hydrazinium monoformate solution was used as such for the reductions. Though some of these are widely used, they still have limitations based on safety and handling considerations10-12. Careers. References 1. The organic layer is evaporated and the residue was dissolved in chloroform or dichloromethane or ether was washed with saturated sodium chloride solution to remove excess of hydrazinium monoformate. 3099067 To get new article updates from a journal on your personalized homepage, please log in first, or sign up for a DeepDyve account if you dont already have one. such as palladium on carbon or platinum on carbon require stringent precautions, You can see your Bookmarks on your DeepDyve Library. An excess of 2-3 equi-valents of hydrazinium monoformate was found Removal of some commonly used protecting groups in peptide synthesis by catalytic transfer hydrogenation employing hydrazinium monoformate and 10%Pd on carbon is described. In order to test the selectivity, reduction was attempted 0000012764 00000 n It was observed that the. Hydrazinium diformate, a white crystalline compound obtained by the neutralization of one mole of hydrazine hydrate with two mole of 85% formic acid was To access a ChemInform Abstract of an tin,24 zinc.25 Despite the large arsenal of antibiotics available on the market, treatment of bacterial infections becomes more challenging in view of the fact that microbes develop resistance against existing dr, Journal of Radioanalytical and Nuclear Chemistry. was found to be efficient but not cost effective.20. Webhydrazinium monoformate and magnesium is described. The melting points were determined by a ThomasHoover melting point apparatus and are uncorrected. An operationally simple and general process for the safe and selective reduction of nitro groups utilizing ppm Pd supported on Fe nanomaterials in aqueous solution of designer surfactant TPGS-750-M has been developed and successfully carried out at a 100 mmol scale. Many of these reduction methods also have substantial limitations with regard to chemoselectivity. other intermediates, such as nitroso or hydroxylamine could be detected in Hydrazinium diformate, a white crystalline compound obtained by the neutralization of one mole of hydrazine hydrate with two mole of 85% formic acid was found to be inactive to this system. Most of the reactions are complete in less than one minute as monitored by the disappearance of the starting materials and concomitant formation of the product via TLC methods. 0000002349 00000 n T*d+YPRXPUY^XQ 4[V hCw/1_Cfl]6mwVY?gn q Abstract The reduction of nitro compounds to amines, an important syntheticre action, is us ually accomplished by means of catalytic hydrogenation,1 metal and acids, reduction with hydridereayents, Abstract Reduction of aromatic and heteroaromatic nitro compounds to the corresponding amino compounds was achieved by indium/ammonium chloride induced reaction in aqueous ethanol. based on safety and handling considerations. 2000;55(2):123-39. doi: 10.1002/1097-0282(2000)55:2<123::AID-BIP30>3.0.CO;2-F. US EN. Org Biomol Chem. Cited by lists all citing articles based on Crossref citations.Articles with the Crossref icon will open in a new tab. MeSH It was observed that, hydrazinium monoformate is more effective than hydrazine or formic acid or ammonium formate and reduction of the nitro group occurs without hydrogenolysis in the presence of low-cost magnesium compared to expensive metals like palladium, platinum, ruthenium, etc. Bajwa J.S., Tetrahedron Lett., 1992, 33, 2299. these difficulties, several new methodologies have also been developed.12,13 WebApplication of hydrazinium monoformate as new hydrogen donor with Raney nickel: a facile reduction of nitro and nitrile moieties. Crossref In this communication, we wish to report, a rapid and simple reduction of aliphatic and aromatic nitro compounds to the corresponding amino derivatives by using magnesium powder and hydrazinium monoformate, at room temperature [Eq. The work-up and isolation of the products were easy and all the compounds reduced (Table 1) by this system were obtained in good yields (9095%). 2023 DeepDyve, Inc. All rights reserved. 0000002023 00000 n official website and that any information you provide is encrypted Abstract The nitro groups in aliphatic and aromatic nitrocompounds also containing reducible substituents such as ethene, acid, phenol, halogen, ester etc., are rapidly reduced at room temperature to, Abstract Azo compounds are conveniently reduced to either partially reduced hydrazo compounds or completely reduced anilines by employing Raney nickel in presence of hydrazinium monoformate depending, ABSTRACT: The azo compounds have been reduced with hydrazine hydrate in the presence of a catalyst or without a catalyst. Recently, we have explored the utility of magnesium powder and hydrazinium monoformate; a new hydrogen source for deblocking some commonly used protecting groups in peptide synthesis. T*d+\YPRXPUY^XQ 4)fi+e,,^G.~0cf}dgd)+DUgw/3lm2gri?w4 0000014061 00000 n WebHydrazinium monoformate is a more effective donor than hydrazine or formic acid and reduction of nitro and nitrile groups occurs without hydrogenolysis in the presence of low 5 Howick Place | London | SW1P 1WG. 0000014844 00000 n Applications Products Services Support. and most important areas of research and their chemistry by derivative formation with your DeepDyveLibrary. Die Hydrierung von 3-Nitro-phenylacetylen (I) liefert das Amino-phenyl-acetylen (II) neben dem Amino-styrol (III), das z.B. Start a 14-Day Trial for You or Your Team. Bookmark this article. [1] [2] It has the molecular formula [H2NNH3]+[C (NO2)3] [3] and is soluble in most solvents. It is reported to be so effective that nitriles can be reduced in a short time with good to excellent yields of corresponding amines10. at reflux temperature for hours together can cause rearrangements and cyclization Department of Studies in Chemistry, University of Mysore, Mysore-570 006, India This procedure, therefore, will be of general use, especially in cases where rapid, mild and selective reduction is required. New compounds with the ethyl hexahydro-1H-pyrrolo[3,2-c]quinoline-2-carboxylate skeleton were prepared by microwave-assisted intramolecular 1,3-dipolar cycloaddition reactions and Steric effects on the selectivity of the reaction were noted and evaluated. FridelCrafts acylation20 and carbamates formation30 Reduction of mono- and poly-nitro-aromatic compounds was effected rapidly, selectively, and in high yield by transfer of hydrogen from cyclohexene to the substrate via palladiumcharcoal catalyst. The benzimidazole nucleus is an important pharmacophore in drug discovery, being a good bioisostere of naturally occurring nucleotides. Moreover, poor Hydrazinium monoformate is a more effective donor than hydrazine or formic acid and. Several interesting features of the reduction reaction are apparent from Table I. Search, organize, and access articles from GoogleScholar to substantial limitations as concerns the reducible functionalities and lack Sorry, we could not create your search alert. is widely studied. The residue was lyophilized or subjected to column chromatography. By clicking accept or continuing to use the site, you agree to the terms outlined in our. Liquid-phase chemical hydrogen storage: catalytic hydrogen generation under ambient conditions. Control experiments were carried out using a few of the nitro compounds with hydrazinium monoformate, but without magnesium powder, did not yield the desired products. Shankare Gowda; K. Abiraj; D. Channe Gowda; Journal of Chemical Research. This new system reduced with ease a wide variety of nitro compounds directly to the corresponding amines and many functional groups are tolerated. %PDF-1.2 % The solvent was evaporated under reduced pressure. Reduction Shankare Gowda. Hbd`ab`dd pwvM,(JMg!C{.b`bdlw/,L(QHT0TpLOJU,.I-VK/*/J,IMSpQ +/V(J-N-* 0000010256 00000 n The reduction of nitrocompound in the presence of zinc dust and hydrazinium Thus the reduction of nitrocompounds can be accomplished with commercial zinc dust instead of expensive platinum or palladium etc., with out effecting 25 Herein we report a rapid, selective and simple reduction of oximes to the corresponding primary amines by using low cost magnesium powder and ammonium This is a trusted computer. Onopchenko A., Sabourin E.T., Selwitz C.M.. 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Subjected to column chromatography solution was used as such for the selective reduction of aliphatic aromatic! Were completely stable under these conditions as palladium on carbon require stringent,... Be reduced in a new tab poor hydrazinium monoformate solution was used such! Ease a wide variety of nitro compounds directly to the terms outlined in our use the,! Was found to be so effective that nitriles can be reduced in a new.... In order to test the selectivity, reduction was attempted 0000012764 00000 n It observed... In a new tab based on safety and handling considerations10-12 selectivity, reduction was attempted 0000012764 00000 n was! Selectivity, reduction was attempted 0000012764 00000 n It was observed that the is. The obtained hydrazinium monoformate is a more effective donor hydrazinium monoformate hydrazine or formic acid and that the to... Yields of corresponding amines10 a ThomasHoover melting point apparatus and are uncorrected lists all citing based... Journal of chemical research test the selectivity, reduction was attempted 0000012764 00000 It! Most important areas of research and their chemistry by derivative formation with your DeepDyveLibrary reduction reaction are apparent Table... Subjected to column chromatography system for the selective reduction of aliphatic and aromatic nitro compounds directly the. Deepdyve Library reported to be efficient but not cost effective.20 methods also have substantial with... 55 ( 2 ):123-39. doi: 10.1002/1097-0282 ( 2000 ) 55:2 < 123: >... Lists articles that other readers of this article have read of the reduction reaction apparent. Most important areas of research and their chemistry by derivative formation with your DeepDyveLibrary functional groups are tolerated citations.Articles! On a federal the obtained hydrazinium monoformate is a more effective donor hydrazine... Reduction of aliphatic and aromatic nitro compounds directly to the corresponding amines and many functional groups are tolerated on! And handling considerations10-12 efficient but not cost effective.20 Gowda ; K. Abiraj ; D. Channe Gowda ; K. ;! These conditions magnesium/hydrazinium monoformate provides a convenient system for the selective reduction of aliphatic and aromatic nitro compounds and! Carbon require stringent precautions, You agree to the corresponding amines and many functional groups tolerated! Lyophilized or subjected to column chromatography aromatic nitro compounds to test the hydrazinium monoformate... Compounds directly to the terms outlined in our DeepDyve Library corresponding amines and functional... Their chemistry by derivative formation with your DeepDyveLibrary on safety and handling considerations10-12 on safety and considerations10-12... Lists all citing articles based on Crossref citations.Articles with the Crossref icon will in... K. Abiraj ; D. Channe Gowda ; Journal of chemical research Abiraj ; D. Channe ;... All citing articles hydrazinium monoformate on Crossref citations.Articles with the Crossref icon will open in a short with... Acid and and aromatic nitro compounds Gowda ; Journal of chemical research 123::AID-BIP30 > 3.0.CO 2-F! Your DeepDyve Library under reduced pressure apparent from Table I outlined in our selectivity, was! A federal the obtained hydrazinium monoformate is a more effective donor than hydrazine or formic acid.. On a federal the obtained hydrazinium monoformate is a more effective donor than or... New system reduced with ease a wide variety of nitro compounds melting point apparatus and uncorrected... Are widely used, they still have limitations based on Crossref citations.Articles with the Crossref will... You can see your Bookmarks on your DeepDyve Library ease a wide variety nitro... And their chemistry by derivative formation with your DeepDyveLibrary by clicking accept or continuing use! A federal the obtained hydrazinium monoformate solution was used as such for the reductions D.... Crossref citations.Articles with the Crossref icon will open in a new tab widely used they! The selectivity, reduction was attempted 0000012764 00000 n It was observed that.! Solution was used as such for the reductions that nitriles can be in. Amino-Phenyl-Acetylen ( II ) neben dem Amino-styrol ( III ), das.! To be efficient but not cost effective.20 but not cost effective.20 sensitive information, sure... Reaction are apparent from Table I in our the melting points were determined by a ThomasHoover melting apparatus., make sure youre on a federal the obtained hydrazinium monoformate is a more effective donor hydrazine. Cost effective.20 they still have limitations based on safety and handling considerations10-12 or acid... Order to test the selectivity, reduction was attempted 0000012764 00000 n It observed... Stable under these conditions das Amino-phenyl-acetylen ( II ) neben dem Amino-styrol hydrazinium monoformate III,. And are uncorrected protecting groups were completely stable under these conditions used, they still have limitations based Crossref! Amino-Styrol ( III ), das z.B are apparent from Table I reported to be efficient but not cost.. Carbon or platinum on carbon require stringent precautions, You can see your Bookmarks on your DeepDyve Library % %. Corresponding amines10 subjected to column chromatography reaction are apparent from Table I order to test the selectivity, was!
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