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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 5
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Original Articles

Modified Pyridinium Chlorochromate Oxidation of Aldehydes to Carbamoyl Azides/Acyl Azides or Carboxylic Acids

P. Satyanarayana Reddy Departments of Molecular Genetics and Pharmacology, University of Texas Health Science Center, Dallas, Texas, 75235, USA
,
Pendri Yadagiri Departments of Molecular Genetics and Pharmacology, University of Texas Health Science Center, Dallas, Texas, 75235, USA
,
Sun Lumin Departments of Molecular Genetics and Pharmacology, University of Texas Health Science Center, Dallas, Texas, 75235, USA
,
Dong-Soo Shin Departments of Molecular Genetics and Pharmacology, University of Texas Health Science Center, Dallas, Texas, 75235, USA
&
J. R. Falck Departments of Molecular Genetics and Pharmacology, University of Texas Health Science Center, Dallas, Texas, 75235, USA
Pages 545-551 | Published online: 06 Dec 2006

Citations (39)

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Paul Fr⊘Syen. (1996) One-Flask Conversion of Carboxylic Acids into Carbamoyl Azides. Synthetic Communications 26:24, pages 4549-4561.
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Articles from other publishers (38)

Liyan Song, Yufei Meng, Tongchao Zhao, Lifang Liu, Xiaohong Pan, Binbin Huang, Hongliang Yao, Ran Lin & Rongbiao Tong. (2024) Unified and green oxidation of amides and aldehydes for the Hofmann and Curtius rearrangements. Green Chemistry 26:1, pages 428-438.
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Devaneyan Joseph & Sunwoo Lee. (2022) Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane. Organic Letters 24:33, pages 6186-6191.
Crossref
Kotaro Ishihara, Takayuki Shioiri & Masato Matsugi. (2022) Synthesis of carbamoyl azides via the Lossen rearrangement utilizing diphenyl phosphorazidate. Tetrahedron Letters 95, pages 153727.
Crossref
Zvi RappoportKlaus Banert. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups 1 38 .
Vinod K. Yadav, Vishnu P. Srivastava & Lal Dhar S. Yadav. (2016) Visible light induced azidation of aldehydic C–H with carbon tetrabromide and sodium azide. Tetrahedron Letters 57:23, pages 2502-2505.
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Yukino Shinomoto, Akira Yoshimura, Hisato Shimizu, Mutsumi Yamazaki, Viktor V. Zhdankin & Akio Saito. (2015) Tetra- n -butylammonium Iodide Catalyzed C–H Azidation of Aldehydes with Thermally Stable Azidobenziodoxolone . Organic Letters 17:21, pages 5212-5215.
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Batool AkhlaghiniaHamed Rouhi-Saadabad. (2013) Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid–triphenylphosphine system. Canadian Journal of Chemistry 91:3, pages 181-185.
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Najmeh Nowrouzi & Mohammad Zareh Jonaghani. (2012) One-pot, direct synthesis of acyl azides from carboxylic acids using Ph2PCl/I2/NaN3 reagent system. Chinese Chemical Letters 23:4, pages 442-445.
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Tarek A Salama, Saad S Elmorsy, Abdel-Galil M Khalil & Mohamed A Ismail. (2011) Silicon-mediated Direct Conversion of Acyl Chlorides to Carbamoyl Azides or/and Tetrazolinones under Mild Conditions. Chemistry Letters 40:10, pages 1149-1151.
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S. Sundaram & P.S. RaghavanSundaram Srinivasan & Raghavan Seshan. 2011. Chromium -VI Reagents: Synthetic Applications. Chromium -VI Reagents: Synthetic Applications 19 46 .
Klaus Banert, Christian Berndt, Samia Firdous, Manfred Hagedorn, Young‐Hyuk Joo, Tobias Rüffer & Heinrich Lang. (2010) Extremely Simple but Long Overlooked: Generation of α‐Azido Alcohols by Hydroazidation of Aldehydes. Angewandte Chemie International Edition 49:52, pages 10206-10209.
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Klaus Banert, Christian Berndt, Samia Firdous, Manfred Hagedorn, Young‐Hyuk Joo, Tobias Rüffer & Heinrich Lang. (2010) Überaus einfach, doch lange übersehen: die Erzeugung von α‐Azidoalkoholen durch Hydroazidierung von Aldehyden. Angewandte Chemie 122:52, pages 10404-10407.
Crossref
Xiao‐Qiang Li, Wei‐Kun Wang & Chi Zhang. (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. Advanced Synthesis & Catalysis 351:14-15, pages 2342-2350.
Crossref
Hassan M. Badawi. (2008) MP2, MP3 and MP4 versus DFT-B3LYP energies and vibrational assignments of near-planar carbamoyl azide and ketene. Journal of Molecular Structure 888:1-3, pages 379-385.
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Nitin D. Arote & Krishnacharya G. Akamanchi. (2007) Direct conversion of aldehydes to acyl azides using tert-butyl hypochlorite. Tetrahedron Letters 48:32, pages 5661-5664.
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Giovanni Piancatelli & Frederick A. Luzzio. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Elena Gómez-Sánchez & José Marco-Contelles. (2005) Synthesis and transformations of alkyl N-(1-cyclohex-3-enyl)carbamates prepared from cyclohex-3-ene carboxylic acid via Curtius rearrangement. Tetrahedron 61:5, pages 1207-1219.
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O.V. Denisko. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 453 493 .
V.K. Gumaste & A.R.A.S. Deshmukh. (2004) One-pot preparation of dialkylcarbamoyl azides from tertiary amines using triphosgene and sodium azide. Tetrahedron Letters 45:35, pages 6571-6573.
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D.Subhas Bose & A.V.Narsimha Reddy. (2003) Iodine(V) reagents in organic synthesis. Dess–Martin periodinane mediated efficient one-pot oxidation of aldehydes to acyl azides. Tetrahedron Letters 44:17, pages 3543-3545.
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Rodney A. Fernandes & Pradeep Kumar. (2003) PCC-mediated novel oxidation reactions of homobenzylic and homoallylic alcohols. Tetrahedron Letters 44:6, pages 1275-1278.
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R.H. Tale & K.M. Patil. (2002) 3,4,5-Trifluorobenzeneboronic acid: a mild and versatile catalyst for the one-pot synthesis of acyl azides from carboxylic acids. Tetrahedron Letters 43:52, pages 9715-9716.
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B.P. Bandgar & S.S. Pandit. (2002) Synthesis of acyl azides from carboxylic acids using cyanuric chloride. Tetrahedron Letters 43:18, pages 3413-3414.
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V.K. Gumaste, B.M. Bhawal & A.R.A.S. Deshmukh. (2002) A mild and efficient method for the preparation of acyl azides from carboxylic acids using triphosgene. Tetrahedron Letters 43:7, pages 1345-1346.
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Patrick Meffre, Laurence Gauzy, Eric Branquet, Philippe Durand & François Le Goffic. (1996) Synthesis of optically active β,γ-alkynylglycine derivatives. Tetrahedron 52:34, pages 11215-11238.
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. 1996. Comprehensive Heterocyclic Chemistry II. Comprehensive Heterocyclic Chemistry II 685 794 .
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Patrick Meffre, Laurence Gauzy, Chantal Perdigues, Florence Desanges-Levecque, Eric Branquet, Philippe Durand & François Le Goffic. (1995) En route to optically active ethynylglycine derivatives. Tetrahedron Letters 36:6, pages 877-880.
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Hilman Affandi, Aristea V. Bayquen & Roger W. Read. (1994) Direct conversion of carboxylic acids into carbamoyl azides. Tetrahedron Letters 35:17, pages 2729-2732.
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Jong Gun Lee & Ki Hoon Kwak. (1992) Oxidation of aldehydes to acyl azides by chromic anhydride-azidotrimethylsilane. Tetrahedron Letters 33:22, pages 3165-3166.
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Steven V. Ley & Andrew Madin. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 251 289 .
László Markó. (1991) Transition metals in organic synthesis: hydroformylation, reduction, and oxidation. Journal of Organometallic Chemistry 404:1-3, pages 325-504.
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P. S. REDDY, P. YADAGIRI, S. LUMIN, D.‐S. SHIN & J. R. FALCK. (2016) ChemInform Abstract: Modified Pyridinium Chlorochromate Oxidation of Aldehydes to Carbamoyl Azides/Acyl Azides or Carboxylic Acids.. ChemInform 19:40.
Crossref
Kotaro Ishihara, Takayuki Shioiri & Masato Matsugi. (2022) Synthesis of Carbamoyl Azides Via The Lossen Rearrangement Utilizing Diphenyl Phosphorazidate. SSRN Electronic Journal.
Crossref

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