Carbamoyl Azides Research Articles

ChemInform Abstract: Simple and Mild One‐Pot Synthesis of Dipeptidyl Ureas via Carbamoyl Azides of α‐N‐Protected Amino Acids.

ChemInform Abstract: Simple and Mild One‐Pot Synthesis of Dipeptidyl Ureas via Carbamoyl Azides of α‐N‐Protected Amino Acids.

ChemInform Abstract: Different Reactivity of Hydroxylamine with Carbamoyl Azides and Carbamoyl Cyanides: Synthesis of Hydroxyureas and Carbamoyl Amidoximes.

AbstractTreatment of carbamoyl azides with hyrdroxylamine allows a new and convenient access to hydroxyureas.

Study of the Reaction between Carbamoyl Azides of α‐N‐Protected Amino Acids and Hydrazine Monohydrate

AbstractTwo simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α‐N‐protected amino acids and hydrazine monohydrate: 4‐[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1‐[(alkoxycarbonylamino)(alkyl)methyl‐carbamoyl]‐4‐[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI–MS–MS spectra reveal some interesting common features.

Different Reactivity of Hydroxylamine with Carbamoyl Azides and Carbamoyl Cyanides: Synthesis of Hydroxyureas and Carbamoyl Amidoximes

The carbamoylating agents carbamoyl azides and carbamoyl cyanides (aka cyanoformamides) react with hydroxylamine in different ways, leading in the first case to N-hydroxyureas and, in the case of carbamoyl cyanides, to carbamoyl amidoxime derivatives. The synthetic procedure developed for the latter type of compound, which represents an interesting precursor for heterocyclic structures, allowed the highly efficient preparation of a wide selection of examples. The Z configuration of the double bond in the amidoxime moiety was proposed on the basis of comparison between experimental and calculated (13)C and (15)N NMR chemical shift values for the isopropyl and benzyl derivatives.

ChemInform Abstract: One‐Pot Synthesis of Carbamoyl Azides Directly from Primary Alcohols and Oxidation of Secondary Alcohols to Ketones Using Iodobenzene Dichloride in Combination with Sodium Azide.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A Convenient Synthesis of Unsymmetrically Substituted Ureas via Carbamoyl Azides of α‐N‐Protected Amino Acids

AbstractA simple and efficient two‐step synthesis of unsymmetrically substituted ureas containing an amino acid derivative is reported. The procedure involves the reaction between the carbamoyl azides of α‐N‐protected amino acids and ammonium hydroxide or a primary or a secondary amine. The reaction proved to be very fast (0.5 h) with small, highly reactive ammonium hydroxide and slower (4 h) with sterically hindered tert‐butylamine. The 1H NMR spectra of the synthesized, new, unsymmetrical ureas carried out in [D6]DMSO suggest that the protons in the –αCH–NHCONH–CH– moiety assume a trans conformation. Moreover, analysis of the mass spectra (EI and ESI) revealed some interesting common features. The reported synthesis represents the first example of the potential value of carbamoyl azides as versatile chiral starting materials for many synthetic purposes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

One‐Pot Synthesis of Carbamoyl Azides Directly from Primary Alcohols and Oxidation of Secondary Alcohols to Ketones Using Iodobenzene Dichloride in Combination with Sodium Azide

AbstractAn effective synthesis of carbamoyl azides directly from primary alcohols using iodobenzene dichloride in combination with sodium azide has been developed. Moreover, the same regent combination was also efficient for the oxidation of secondary alcohols to the corresponding ketones.

Controlling hazardous chemicals in microreactors: Synthesis with iodine azide

Aromatic aldehydes have been converted into the corresponding carbamoyl azides using iodine azide. These reactions have been performed safely under continuous flow reaction conditions in microreactors.

Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes

We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.

Iodobenzene Dichloride in Combination with Sodium Azide for the Effective Synthesis of Carbamoyl Azides from Aldehydes

Various aliphatic and aromatic aldehydes are converted into their corresponding carbamoyl azides in good to excellent yields with the use of a combined reagent system of iodobenzene dichloride and sodium azide in acetonitrile under nitrogen.

ChemInform Abstract: Synthesis of Carbamoyl Azides from Primary Amines and Carbon Dioxide under Mild Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Carbamoyl Azides from Primary Amines and Carbon Dioxide under Mild Conditions

Treatment of amines under a carbon dioxide atmosphere with tetramethylphenylguanidine (PhTMG) and diphenylphosphoryl azide (DPPA) in acetonitrile below 0 degrees C provides carbamoyl azides in high to excellent yields. In addition, epimerization is not observed when optically pure alpha-amino esters are used as substrates.

Carbamoyl Azides of α-N-Protected Amino Acids: A Fast and Simple One-Pot Synthesis

A fast and simple one-pot synthesis of carbamoyl azides of α-N-protected amino acids is reported. The procedure involves the reaction between sodium azide and the mixed anhydride obtained from an α-N-protected amino acid and isobutyl chloroformate, in the presence of KH 2 PO 4 . The reaction rate was influenced by the nature of both the α-N-protection and the amino acid side chain. Surprisingly, TERT-butyloxycarbonyl (α- N-Boc) and benzyl-oxycarbonyl (α- N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides.

Radical Azidonation of Aldehydes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Radical azidonation of aldehydes.

Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide at 0-25 degrees C. If the reaction is performed at reflux Curtius rearrangement occurs and carbamoyl azides are obtained in 70-97% yield from the aldehyde. The reaction was shown to have a radical mechanism.

One-Flask Conversion of Carboxylic Acids into Carbamoyl Azides

Abstract Carbamoyl azides can be generated in high yields from the corresponding carboxylic acid and triphenylphosphine by adding NCS, followed by sodium azide and triethylamine hydrochloride.

Direct conversion of carboxylic acids into carbamoyl azides

The novel conversion of carboxylic acids and carboxylic acid chlorides directly in a one-pot process into N-monosubstituted carbamoyl azides, presumably through the intermediacy of isocyanate derivatives following Curtius rearrangement, is described.

ChemInform Abstract: Modified Pyridinium Chlorochromate Oxidation of Aldehydes to Carbamoyl Azides/Acyl Azides or Carboxylic Acids.

AbstractThe aldehydes (I) are oxidized with pyridinium chlorochromate in the presence of sodium azide (II) to produce the carbamoyl azides (III) and the acyl azides (IV).

The photolysis of carbamoyl azides in the presence of carbodiimides

The photolysis of carbamoyl azides in the presence of carbodiimides

The Reactions of Carbamoyl Azides with Sulfur Nucleophiles

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Reactions of Carbamoyl Azides with Sulfur NucleophilesVictor J. Bauer, William J. Fanshawe, and S. R. SafirCite this: J. Org. Chem. 1966, 31, 10, 3440–3441Publication Date (Print):October 1, 1966Publication History Published online1 May 2002Published inissue 1 October 1966https://doi.org/10.1021/jo01348a529RIGHTS & PERMISSIONSArticle Views193Altmetric-Citations12LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (312 KB) Get e-Alerts Get e-Alerts