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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 11
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Original Articles

A Convenient Procedure for the Formylation of Amines and Alcohols Using Cyanomethyl Formate

J. Deutsch Centre of Selective Organic Synthesis, Berlin-Adlershof Rudower Chaussee 5, O-1199, Berlin, Germany
&
H.-J. Niclas Centre of Selective Organic Synthesis, Berlin-Adlershof Rudower Chaussee 5, O-1199, Berlin, Germany
Pages 1561-1568 | Received 04 Jan 1993, Published online: 23 Sep 2006

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Manas Chakrabarty, Shampa Khasnobis, Yoshihiro Harigaya & Yaeko Konda. (2000) Neat Formic Acid: an Excellent N-Formylating Agent for Carbazoles, 3-Alkylindoles, Diphenylamine and Moderately Weak Nucleophilic Anilines. Synthetic Communications 30:2, pages 187-200.
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LilianaR. Orelli, MaríaB. Garcia, Fernando Niemevz & IsabelA. Perillo. (1999) Selective Monoformylation Of 1,3-Diaminopropane Derivatives. Synthetic Communications 29:11, pages 1819-1833.
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N. Iranpoor, H. Firouzabadi & M.A. Zolfigol. (1998) Selective Acetylation of Primary Alcohols: Acetyl and Formyl Transfer Reactions with Copper(II) Salts. Synthetic Communications 28:11, pages 1923-1934.
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SureshC. Suri, StephenL. Rodgers, K.V. Radhakrishnan & Vijay Nair. (1996) DMF As a Formate Anion Equivalent: Formolysis of Tosylates in Aqueous DMF1 . Synthetic Communications 26:5, pages 1031-1039.
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Articles from other publishers (21)

Mohammad Jahirul Islam, Kyoung Chul Park, Olivia M. Manley, Mark D. Smith, Thomas M. Makris & Dmitry V. Peryshkov. (2023) Room-Temperature Aerobic C–CN Bond Activation in Nickel(II) Cyanomethyl Dicarboranyl Complex. Organometallics 42:15, pages 1997-2004.
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Kosuke Kato, Kazutada Ikeuchi, Takahiro Suzuki & Keiji Tanino. (2022) Total Synthesis of 2-Isocyanoallopupukeanane: Construction of Caged Skeleton by Intramolecular Alkylation of Bromonitriles. Organic Letters 24:35, pages 6407-6411.
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Runjhun Tandon, Shripad Patil, Nitin Tandon & Pushpendra Kumar. (2022) Magnetically Recyclable Silica-Coated Magnetite-Molybdate Nanocatalyst and its Applications in N-Formylation Reactions Under Solvent-Free Conditions. Letters in Organic Chemistry 19:8, pages 616-626.
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Mahmoud Nasrollahzadeh, Narjes Motahharifar, Mohaddeseh Sajjadi, Amir Moradzadeh Aghbolagh, Mohammadreza Shokouhimehr & Rajender S. Varma. (2019) Recent advances in N -formylation of amines and nitroarenes using efficient (nano)catalysts in eco-friendly media . Green Chemistry 21:19, pages 5144-5167.
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Robert S.L. Chapman, Molly Francis, Ruth Lawrence, Joshua D. Tibbetts & Steven D. Bull. (2018) Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols. Tetrahedron 74:44, pages 6442-6452.
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Simon Bendt Christensen, Anna Mette Hansen & Henrik Franzyk. (2017) On-resin N-formylation of peptides: a head-to-head comparison of reagents in solid-phase synthesis of ligands for formyl peptide receptors. Journal of Peptide Science 23:5, pages 410-415.
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Guy Crépin Enoua, Günther Lahm, Georg Uray & Wolfgang Stadlbauer. (2014) Syntheses and Fluorescent Properties of 6-Methoxy-2-oxoquinoline-3,4-dicarbonitriles and 6,7-Dimethoxy-2-oxoquinoline-3,4-dicarbonitriles. Journal of Heterocyclic Chemistry 51:S1, pages E263-E275.
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Davood Habibi, Mahmoud Nasrollahzadeh & Hesam Sahebekhtiari. (2013) Green synthesis of formamides using the Natrolite zeolite as a natural, efficient and recyclable catalyst. Journal of Molecular Catalysis A: Chemical 378, pages 148-155.
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Chunyang Jin, Scott E. Fix, John A. Kepler & C. Edgar Cook. (2012) Synthesis and antihormonal properties of novel 11β-benzoxazole-substituted steroids. Bioorganic & Medicinal Chemistry Letters 22:4, pages 1705-1708.
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Sang-Hyuk Yeo, Hyun-Ju Seo & Dong-Yeol Lim. (2011) Synthesis of Halicylindramide A Mimetics Containing Lactone Isosteres. Bulletin of the Korean Chemical Society 32:spc8, pages 2916-2920.
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Rostami AMIN, Khazaei ARDESHIR, Alavi-Nik HEIDAR ALI & Toodeh-Roosta ZAHRA. (2011) Formylation of Alcohol with Formic Acid under Solvent-Free and Neutral Conditions Catalyzed by Free I2 or I2 Generated in situ from Fe(NO3)3·9H2O/NaI. Chinese Journal of Catalysis 32:1-2, pages 60-64.
Crossref
G. V. Boyd. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
Jens Deutsch, Reinhard Eckelt, Angela Köckritz & Andreas Martin. (2009) Catalytic reaction of methyl formate with amines to formamides. Tetrahedron 65:50, pages 10365-10369.
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Hyunju Seo & Dongyeol Lim. (2008) Total Synthesis of Halicylindramide A. The Journal of Organic Chemistry 74:2, pages 906-909.
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Habib Firouzabadi, Nasser Iranpoor & Soghra Farahi. (2008) Solid trichlorotitanium(IV) trifluoromethanesulfonate TiCl3(OTf) catalyzed efficient acylation of ?OH and ?SH: Direct esterification of alcohols with carboxylic acids and transesterification of alcohols with esters under neat conditions. Journal of Molecular Catalysis A: Chemical 289:1-2, pages 61-68.
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Gerald L. Newton, Philong Ta & Robert C. Fahey. (2005) A Mycothiol Synthase Mutant of Mycobacterium smegmatis Produces Novel Thiols and Has an Altered Thiol Redox Status . Journal of Bacteriology 187:21, pages 7309-7316.
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Ram N Ram & Nabin Kumar Meher. (2002) Selective formylation of alcohols in the presence of phenols with chloral. Tetrahedron 58:15, pages 2997-3001.
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David R. Hill, Chi-Nung Hsiao, Ravi Kurukulasuriya & Steven J. Wittenberger. (2001) 2,2,2-Trifluoroethyl Formate:  A Versatile and Selective Reagent for the Formylation of Alcohols, Amines, and N -Hydroxylamines . Organic Letters 4:1, pages 111-113.
Crossref
Iraj Mohammadpoor-Baltork, Ahmad Reza Khosropour & Hamid Aliyan. (2019) A Convenient and Chemoselective Acetylation and Formylation of Alcohols and Phenols Using Acetic Acid and Ethyl Formate in the Presence of Bi(III) Salts. Journal of Chemical Research 2001:7, pages 280-282.
Crossref
J. Deutsch, W. Duczek & Hans-Joachim Niclas. (1996) Formyloxy-acetonitrile - a reagent for convenientN- andO-formylations. Journal f�r Praktische Chemie/Chemiker-Zeitung 338:1, pages 488-490.
Crossref
J. DEUTSCH & H.‐J. NICLAS. (2010) ChemInform Abstract: A Convenient Procedure for the Formylation of Amines (II), (IV) and Alcohols (VI) Using Cyanomethyl Formate (I).. ChemInform 25:3.
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