- Iodine(V) reagents in organic synthesis. Dess-Martin periodinane mediated efficient one-pot oxidation of aldehydes to acyl azides
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A mild, efficient and general method for the one-step preparation of acyl azides from aldehydes using Dess-Martin periodinane and sodium azide is described.
- Bose, D. Subhas,Reddy, A. V. Narsimha
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Read Online
- Oxidation of aldehydes to acyl azides using triazidochlorosilane (TACS)-active manganese dioxide reagent
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Triazidochlorosilane (TACS)-active manganese dioxide is a new and versatile system for the efficient oxidation of aldehydes to the corresponding acyl azides at 0°C, in dichloromethane.
- Elmorsy, Saad S.
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Read Online
- Synthesis of Acyl Phosphoramidates Employing a Modified Staudinger Reaction
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A one-step synthesis of acyl phosphoramidates from a variety of functionalized acyl azides has been developed employing trimethylsilyl chloride as an activating agent in a modified Staudinger reaction. The methodology was further adapted to include the in situ generation of the acyl azides from a diverse selection of carboxylic acids and hydrazide starting synthons. The reaction scope was extended to include the synthesis of imidodiphosphates and the natural product Microcin C.
- Currie, Iain,Sleebs, Brad E.
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supporting information
p. 464 - 468
(2021/02/03)
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- Suppressive activities of KC1–3 on HMGB1-mediated septic responses
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In the present study, several decursin analogues (KC1–3) were synthesized and evaluated in terms of their anti-septic activities on high mobility group box 1 (HMGB1)-mediated septic responses and survival rate in a mouse model of sepsis. KC1 and KC3, but not KC2, significantly reduced HMGB1 release in lipopolysaccharide (LPS)-activated human umbilical vein endothelial cells (HUVECs) and attenuated the cecal ligation and puncture (CLP)-induced release of HMGB1. Additionally, in vitro analyses revealed that KC1 and KC3 both alleviated HMGB1-mediated vascular disruptions and inhibited hyperpermeability in mice, and in vivo analyses revealed that KC1 and KC3 reduced sepsis-related mortality and tissue injury. Taken together, the present results suggest that KC1 and KC3 both reduced HMGB1 release and septic mortality and, thus, may be useful for the treatment of sepsis.
- Lee, Wonhwa,Yuseok,Lee, Changhun,Jeong, So Yeon,Lee, Jee-Hyun,Baek, Moon-Chang,Song, Gyu-Yong,Bae, Jong-Sup
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p. 260 - 268
(2019/03/04)
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- Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
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Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.
- Giancotti, Gilda,Cancellieri, Michela,Balboni, Andrea,Giustiniano, Mariateresa,Novellino, Ettore,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
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supporting information
p. 56 - 68
(2018/03/06)
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- Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to: In situ -generated ortho -quinone methides
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The first organocatalytic asymmetric reaction of acyclic enecarbamates with o-quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2,3,4-trisubstituted chroman products.
- Gharui, Chandan,Singh, Shreya,Pan, Subhas Chandra
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p. 7272 - 7276
(2017/09/25)
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- Decursinol-carbamate derivatives, and pharmaceutical composition containing the same for preventing or treating cancer
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The present invention relates to a decursinol carbamate derivative represented by chemical formula 1, and to a composition for preventing or treating cancer containing the same. The decursinol carbamate derivative shows excellent activity of inhibiting a
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Paragraph 0260-0266
(2017/02/02)
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- Visible light C-H amidation of heteroarenes with benzoyl azides
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Benzoyl azides were used for the direct and atom economic C-H amidation of electron rich heteroarenes in the presence of phosphoric acid, a photocatalyst and visible light. Hetero-aromatic amides are obtained in good yields at very mild reaction conditions with dinitrogen as the only by-product. The reaction allows the use of aryl-, heteroaryl- or alkenyl acyl azides and has a wide scope for heteroarenes, including pyrroles, indole, furan, benzofuran and thiophene giving good regio-selectivities and yields.
- Brachet,Ghosh,Ghosh,K?nig
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supporting information
p. 987 - 992
(2015/02/19)
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- Thermal-induced dimerization cyclization of ethyl N-(styrylcarbamoyl) acetates: Formation of 4-hydroxy-2(1H)-pyridone-3- carboxamide derivatives
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Thermal-induced dimerization cyclization of ethyl N-(styrylcarbamoyl) acetate derivatives has been investigated, leading to 4-hydroxy-2(1H)-pyridone- 3-carboxamide derivatives with good yields in diphenyl ether on 200-210 °C. Ethyl N-(styrylcarbamoyl)acet
- Zhao, Sheng-Yin,Liu, Bao-Shuo,Huang, Jing,Cheng, Shao-Hua,Deng, Yun-Xia,Shao, Zhi-Yu
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supporting information
p. 2066 - 2075
(2014/07/07)
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- Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid-triphenylphosphine system
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A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid-triphenylphosphine, is described.
- Akhlaghinia, Batool,Rouhi-Saadabad, Hamed
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p. 181 - 185
(2013/05/09)
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- Copper-mediated amidation of alkenylzirconocenes with acyl azides: Formation of enamides
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Copper-mediated amidation of alkenylzirconocenes generated in situ from alkynes and zirconocenes with acyl azides is accomplished under mild conditions. The reaction can be used to prepare various enamides.
- Liu, Hailan,Zhou, Yiqing,Yan, Xiaoyu,Chen, Chao,Liu, Qingbin,Xi, Chanjuan
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supporting information
p. 5174 - 5177
(2013/11/06)
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- Synthesis of styryl substituted semicarbazides under microwave irradiation
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A series of styryl substituted semicarbazides were synthesised by reaction of trans-styryl isocyanate, prepared by Curtius rearrangement of cinnamoyl azide, with acid hydrazides under microwave irradiation using a one-pot procedure. The effects of microwa
- Chai, Lan-Qin,Zhang, Hong-Song,Liu, Gang,Huang, Jiao-Jiao,Cheng, Qiao-Qiao
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p. 356 - 358
(2013/07/26)
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- Intramolecular vinylation of secondary and tertiary organolithiums
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Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N′-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates α-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp2 carbon atom, proceeds by a concerted addition-elimination pathway.
- Lefranc, Julien,Fournier, Anne M.,Mingat, Gaelle,Herbert, Simon,Marcelli, Tommaso,Clayden, Jonathan
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supporting information; experimental part
p. 7286 - 7289
(2012/06/16)
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- Synthesis of cinnamic acid-derived phenethyl carbamates and their radical scavenging ability toward DPPH free radicals
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A simple and efficient synthetic detail of cinnamic acid carbamate derivatives and their antioxidant activities was studied. The antioxidant activity of the compounds was measured by standard free radical scavenging assay (DPPH test) as a primary tool. Th
- Hwang, Ki-Jun,Cho, Kwang-Jin,Jung, Nam-Gin,Song, Choon-Ho,Kwang-Joong,Kim, Beom-Tae
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experimental part
p. 136 - 140
(2011/04/22)
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- FeCl36H2O-Catalyzed acceleration of the acylation of sodium azide with n-acylbenzotriazoles
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Catalyzed by ferric chloride hexahydrate (FeCl36H2O), the acylation of sodium azide with N-acylbenzotriazoles was greatly accelerated in a mixed solvent of acetone and water. Thus, good to excellent yields of a variety of acyl azides were obtained at room temperature in a short time. Furthermore, because of the complete conversion of N-acylbenzotriazoles and the easy removal of the by-product, purification by column chromatography was no longer required, which made the protocol suitable for large-scale preparation.
- Zhong, Zhiyun,Hu, Jieling,Wang, Xiaoxia,Liu, Junhua,Zhang, Longfeng
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experimental part
p. 2461 - 2467
(2011/08/05)
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- T3P (propylphosphonic anhydride) mediated conversion of carboxylic acids into acid azides and one-pot synthesis of ureidopeptides
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A general, mild, efficient, and environmentally benign protocol, which makes use of T3P as an acid activating agent for the direct synthesis of acid azides from carboxylic acids is described. Further, the protocol is employed for the one-pot synthesis of α-ureidopeptides starting from N-protected α-amino acids.
- Basavaprabhu,Narendra,Lamani, Ravi S.,Sureshbabu, Vommina V.
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experimental part
p. 3002 - 3005
(2010/07/10)
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- Facile one step synthesis of acyl azides and Nα-Fmoc/Boc/Z protected amino acid azides employing benzotriazole-1-yl-oxy-tris- (dimethylamino)-phosphonium hexafluorophosphate (BOP)
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A simple route for the preparation of acyl azides from the corresponding carboxylic acids employing the peptide-coupling agent BOP is described. The procedure is simple, clean and high yielding. The chemistry is also extended to the preparation of several urethane protected amino acid azides (eight examples) as well.
- Vasantha,Sureshbabu, Vommina V.
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experimental part
p. 812 - 817
(2011/01/04)
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- New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU
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Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.
- Sureshbabu, Vommina V.,Lalithamba,Narendra,Hemantha
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experimental part
p. 835 - 840
(2010/06/20)
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- Simple and facile method for the preparation of vinyl azides
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A synthetic utility of [bis(trifluoroacetoxy)iodo]benzene on α,β-unsaturated carboxylic acid is described. This is the first example of preparation of vinyl azide using α,β-unsaturated carboxylic acids directly by using hypervalent iodine reagent. The adv
- Telvekar, Vikas N.,Takale, Balaram S.,Bachhav, Harshal M.
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scheme or table
p. 5056 - 5058
(2009/12/05)
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- Direct synthesis of acyl azides from carboxylic acids by the combination of trichloroacetonitrile, triphenylphosphine and sodium azide
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Various carboxylic acids were converted into acyl azides in excellent yields by treating with trichloroacetonitrile, triphenylphosphine and sodium azide at room temperature. The reaction was applicable to the preparation of dipeptide without rearrangement.
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 2072 - 2074
(2009/04/07)
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- One-pot synthesis of phenylallyl substituted unsymmetrical ureas under microwave irradiation
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A series of phenylallyl-substituted unsymmetrical ureas were synthesized in a one-pot procedure by reactions of cinnamoyl isocyanate, which was prepared from cinnamoyl azide by Curtius rearrangement, with various aromatic amines, 2-amino-5-aryl-1,3,4-thia
- Chai, Lan-Qin,Chen, Wei-Peng,Wang, Xiao-Qiang,Ge, Jian-Lin
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p. 2491 - 2496
(2008/04/03)
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- Preparation of polyfunctional acyl azides
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(Chemical Equation Presented) A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles is described. The procedure affords acyl azides in good yields and avoids the use of acid activators and NO+ equivalents typically emp
- Katritzky, Alan R.,Widyan, Khalid,Kirichenko, Kostyantyn
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p. 5802 - 5804
(2008/02/09)
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- Discovery of potent, selective, orally active, nonpeptide inhibitors of human mast cell chymase
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A series of β-carboxamido-phosphon(in)ic acids (2) was identified as a new structural motif for obtaining potent inhibitors of human mast cell chymase. For example, 1-naphthyl derivative 5f had an IC50 value of 29 nM and (E)-styryl derivative 6
- Greco, Michael N.,Hawkins, Michael J.,Powell, Eugene T.,Almond Jr., Harold R.,De Garavilla, Lawrence,Hall, Jeffrey,Minor, Lisa K.,Wang, Yuanping,Corcoran, Thomas W.,Di Cera, Enrico,Cantwell, Angelene M.,Savvides, Savvas N.,Damiano, Bruce P.,Maryanoff, Bruce E.
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p. 1727 - 1730
(2008/02/02)
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- Reactions of N-methyl cyclic ketene-N,X-acetals (X = S, O) with isocyanates and isothiocyanate
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Nucleophilic N-methyl cyclic ketene-N,X-acetals (X = S, O) can react with electrophilic aryl isocyanates, vinyl isocyanates and aryl isothiocyanates to form mono-adducts, bis-adducts and spirobicyclic compounds. Georg Thieme Verlag Stuttgart.
- Zhou, Aihua,Cao, Liwei,Li, Haiqing,Liu, Zhuqing,Pittman Jr., Charles U.
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p. 201 - 206
(2007/10/03)
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- Preparation of acyl azides from aromatic carboxylic acids using triphosgene in ionic liquids
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Acyl azides are obtained in high yields from aromatic carboxylic acids and sodium azide at room temperature in ionic liquids using triphosgene as a synthetic auxiliary under mild reaction conditions and with a short reaction time.
- Bao, Weiliang,Wang, Qiang
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p. 700 - 701
(2007/10/03)
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- Synthesis of acyl azides using the Vilsmeier complex
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A facile synthesis of substituted cinnamoyl and benzoyl azides starting from their respective acids using DMF and POCl3 in the presence of sodium azide is reported.
- Sridhar, Radhakrishnan,Perumal, Paramasivan T.
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p. 607 - 611
(2007/10/03)
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- A mild and efficient method for the preparation of acyl azides from carboxylic acids using triphosgene
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An efficient use of triphosgene for the preparation of various acyl azides from carboxylic acids and sodium azide is described.
- Gumaste,Bhawal,Deshmukh
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p. 1345 - 1346
(2007/10/03)
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- Synthesis of acyl azides from carboxylic acids using cyanuric chloride
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A mild, efficient and general method for the preparation of acyl azides from carboxylic acids and sodium azide using cyanuric chloride is described.
- Bandgar,Pandit
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p. 3413 - 3414
(2007/10/03)
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- 3,4,5-Trifluorobenzeneboronic acid: A mild and versatile catalyst for the one-pot synthesis of acyl azides from carboxylic acids
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Acyloxyboron intermediates generated from carboxylic acids and 3,4,5-trifluorobenzeneboronic acid react with sodium azide to furnish the corresponding acyl azides in moderate to good yields.
- Tale,Patil
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p. 9715 - 9716
(2007/10/03)
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- Regioselective cationic reduction of 2-aryl-1-N-(ethoxycarbonyl)enamines to 2-arylethylamine carbamates
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2-Aryl-1-N-carboalkoxyenamines (enamides) are selectively reduced to the corresponding 2-arylethylamine carbamates by Et3SiH in the presence of CF3COOH in excellent yields. The reduction proceeds by addition of hydride at C-1 and the
- Masuno, Makoto N,Molinski, Tadeusz F
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p. 8263 - 8266
(2007/10/03)
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- Unsaturated enamides via organometallic addition to isocyanates: The synthesis of Lansamide-I, Lansiumamides A-C and SB-204900
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Styryl Grignard addition to vinyl isocyanates is employed to prepare the naturally occurring enamides Lansamide-I, Lansiumamides A and B, and SB- 204900; the synthesis of Lansiumamide C is also reported. (C) 2000 Elsevier Science Ltd.
- Stefanuti, Ian,Smith, Stephen A.,Taylor, Richard J. K.
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p. 3735 - 3738
(2007/10/03)
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- Synthesis of acyl azides via polymer-supported reagent
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Acyl azides have been synthesised in high yields and in a state of high purity by reacting acyl chloride with polymer-supported azide ion reagent.
- Thorat, M. T.,Mane, R. B.,Deshmukh, J. G.,Salunkhe, M. M.,Wadgaonkar, P. P.
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p. 186 - 187
(2007/10/02)
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- Preparation of Highly Substituted 2-Pyridones by Reaction of Vinyl Isocyanates and Enamines
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A method for synthesis of highly substituted 2(1H)-pyridones is reported.Vinyl isocyanates, prepared from the corresponding α,β-unsaturated carboxylic acids, undergo cyclization with various enamines to furnish six-membered heterocycles.The methodology is exemplified by numerous examples.Application of this strategy is further illustrated by the synthesis of several aza steroid analogues.
- Rigby, James H.,Balasubramanian, N.
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p. 224 - 228
(2007/10/02)
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- Synthesis of Enamides
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(Z)-3-Arylprop-2-enoic acids can be converted by the Curtius procedure, through the acyl azides, into (Z)-2-arylethenyl isocyanates, which with methanol give methyl (Z)-N-(2-arylethenyl)carbamates.Acylation of the (Z)-enecarbamates, through their anions, leads to methyl (Z)-N-acyl-N-(2-arylethenyl)carbamates, which on treatment with lithium iodide in boiling N,N-dimethylformamide or acetonitrile undergo demethoxycarbonylation to give (Z)-enamides.The stereospecific route to enamides can also be used in the E-series.Treatment of (Z)- or (E)-2-arylethenyl isocyanates with trifluoroacetic acid gives (E)-N-(2-arylethenyl)trifluoroacetamides,the anions of which, with acylating agents, give (E)-enamides directly.
- Brettle, Roger,Mosedale, Alan J.
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p. 2185 - 2196
(2007/10/02)
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- Structure-Reactivity Relationships in Nucleophilic Reactions on Cinnamoyl Azide and Phenyl Cinnamates. Kinetic Stability of the Acyl Azide and Relative Leaving Ability of Nitrogen and Oxygen
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The alkaline hydrolysis and aminolysis of cinnamoyl azide and aryl-substituted phenyl cinnamates and the azidolysis of the phenyl cinnamates have been studied.The positions of the rate-determining steps in the reactions are identified by the structure-reactivity relationships.The enhanced affinity of azide ion for an acyl carbon compared with its basicity is proposed to account for the observed kinetic stability of cinnamoyl azide toward alkaline hydrolysis and aminolysis.Azide ion resists expulsion from the tetrahedral intermediate more than quinuclidine derivatives but less than phenolates.This is explained in terms of the electron withdrawal as well as electron donation by resonance.
- Suh, Junghun,Lee, Byung Hyun
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p. 3103 - 3107
(2007/10/02)
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