{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,23]],"date-time":"2025-10-23T16:41:49Z","timestamp":1761237709948,"version":"build-2065373602"},"reference-count":34,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2010,4,27]],"date-time":"2010-04-27T00:00:00Z","timestamp":1272326400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>N-Methyl-3-acylpyrroles were synthesized via a multicomponent reaction of dimethylacetylene dicarboxylate (DMAD), N-methylhydroxylamine and acylchlorides in the presence of KHCO3. For comparison both conventional and microwave protocols were examined in this procedure. The reaction is clean and gives the products in good to excellent yields under conventional heating conditions at 40 \u00baC in anhydrous dichloromethane.<\/jats:p>","DOI":"10.3390\/molecules15052972","type":"journal-article","created":{"date-parts":[[2010,4,27]],"date-time":"2010-04-27T11:18:19Z","timestamp":1272367099000},"page":"2972-2979","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["A Mild and Facile One-Pot Synthesis of N-Methyl-3-Acyl-Pyrroles"],"prefix":"10.3390","volume":"15","author":[{"given":"Hassan","family":"Valizadeh","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ashraf","family":"Fakhari","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2010,4,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"991","DOI":"10.1016\/S0223-5234(99)00111-7","article-title":"Synthesis and antioxidant activity of new tetraarylpyrroles","volume":"34","author":"Lehuedu","year":"1999","journal-title":"Eur. J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1439","DOI":"10.1016\/j.ejmech.2006.07.009","article-title":"Synthesis and antimicrobial activity of new bromine-rich pyrrole derivatives related to monodeoxypyoluteorin","volume":"41","author":"Raimondi","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2655","DOI":"10.1016\/j.ejmech.2008.11.013","article-title":"Phenylpyrrole derivatives as neural and inducible nitric oxide synthase (nNOS and iNOS) inhibitors","volume":"44","author":"Cara","year":"2009","journal-title":"Eur. J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"516","DOI":"10.1016\/j.snb.2008.09.020","article-title":"Impedance study of the hybrid molecule alginate\u2013pyrrole: Demonstration as host matrix for the construction of a highly sensitive amperometric glucose biosensor","volume":"136","author":"Marks","year":"2009","journal-title":"Sens. Actuat. B. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3587","DOI":"10.1021\/jo9915224","article-title":"Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A","volume":"65","author":"Liu","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5979","DOI":"10.1016\/j.bmcl.2004.10.002","article-title":"Multidrug resistance reversal activity of permethyl ningalin B amide derivatives","volume":"14","author":"Tao","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1401","DOI":"10.1016\/0040-4039(95)00016-6","article-title":"1-Alkyl-3-(1-naphthoyl)pyrroles: A new class of cannabinoid","volume":"36","author":"Lainton","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1016\/S0960-894X(01)80155-4","article-title":"Design, synthesis and pharmacology of cannabimimetic indoles","volume":"4","author":"Huffman","year":"1994","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1911","DOI":"10.1002\/hlca.19690520716","article-title":"Revidierte struktur von verrucarin E. Eine synthese des antibioticums und verwandter \u03b2-acetyl-pyrrol-derivate. Verrucarine und roridine","volume":"52","author":"Tamm","year":"1969","journal-title":"Helv. Chim. Acta"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2229","DOI":"10.1039\/a703421k","article-title":"Approaches to 1,1-disubstituted cinnolin-3-ylio oxides: synthesis and reactivity of a new class of heterocyclic betaines","volume":"2","author":"Langley","year":"1997","journal-title":"J. Chem. Soc. Perkin. Trans."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/0379-6779(89)90517-1","article-title":"New conducting polymers from 3-alkylpyrroles","volume":"28","author":"Ruhe","year":"1989","journal-title":"Synth Met."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Delabouglise, D., Roncali, J., Lemaire, M., and Garnier, F. (1989). Control of the lipophilicity of polypyrrole by 3-alkyl substitution. J. Chem. Soc. Chem. Commun., 475\u2013477.","DOI":"10.1039\/c39890000475"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/S0379-6779(00)00250-2","article-title":"The synthesis of a number of 3-alkyl and 3-carboxy substituted pyrroles; their chemical polymerisation onto poly(vinylidene fluoride) membranes, and their use as gas sensitive resistors","volume":"114","author":"Evans","year":"2000","journal-title":"Synth. Met."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/S0379-6779(98)00169-6","article-title":"Toward intelligent polymers: DNA sensors based on oligonucleotide-functionalized polypyrroles","volume":"100","author":"Garnier","year":"1999","journal-title":"Synth Met."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1039\/a704493c","article-title":"Synthesis of aromatic heterocycles","volume":"1","author":"Gilchrist","year":"1998","journal-title":"J. Chem. Soc. Perkin. Trans."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2283","DOI":"10.1021\/ol006050q","article-title":"A facile synthesis of polysubstituted pyrroles","volume":"2","author":"Dieter","year":"2000","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1021\/ja962173n","article-title":"Reactions of propargyl metallic species generated by the addition of alkynyllithiums to fischer-type carbene complexes","volume":"119","author":"Iwasawa","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6637","DOI":"10.1021\/jo00125a068","article-title":"A new, titanium-mediated approach to pyrroles: First synthesis of lukianol A and lamellarin O dimethyl ether","volume":"60","author":"Furstner","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4551","DOI":"10.1021\/jo00095a034","article-title":"1-Aza-1,3-bis(triphenylphosphoranylidene)propane: A Novel :CHCH2N: Synthon","volume":"59","author":"Katritzky","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4204","DOI":"10.1021\/jo982342h","article-title":"Conversion of aryl methyl ketimines to 2,5-diarylpyrroles using TiCl4\/Et3N","volume":"64","author":"Periasamy","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5383","DOI":"10.1016\/j.tetlet.2006.05.085","article-title":"An approach to the Paal\u2013Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions","volume":"47","author":"Chen","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3501","DOI":"10.1016\/j.tetlet.2005.03.124","article-title":"An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions","volume":"46","author":"Valizadeh","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1081\/SCC-200050942","article-title":"Effect of microwave irradiation on reaction of arylaldehyde derivatives with some active methylene compounds in aqueous media","volume":"35","author":"Valizadeh","year":"2005","journal-title":"Synth. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1666","DOI":"10.1080\/00397910802573163","article-title":"One-pot Wittig and Knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives","volume":"39","author":"Valizadeh","year":"2009","journal-title":"Synth. Commun."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2555","DOI":"10.1080\/10426500214560","article-title":"Solvent free synthesis of coumarins","volume":"177","author":"Shockravi","year":"2002","journal-title":"Phosphorus, Sulfur, Silicon Relat. Elem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1002\/jhet.20","article-title":"Efficient and convenient method for the synthesis of isoxazoles in ionic liquid","volume":"46","author":"Valizadeh","year":"2009","journal-title":"J. Heterocycl. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Valizadeh, H., Heravi, M.M., and Amiri, M. (2009). Unexpected synthesis of N-methylbenzo[d]isoxazolium hydroxides under microwave irradiation conditions. Mol. Divers.","DOI":"10.1007\/s11030-009-9189-x"},{"key":"ref_28","unstructured":"Katritzky, A.R., and Boulton, A.J. (1970). Advances in Heterocyclic Chemistry, Academic Press."},{"key":"ref_29","unstructured":"Katritzky, A.R., and Boulton, A.J. (1970). Advances in Heterocyclic Chemistry, Academic Press."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Katritzky, A., and Ress, C.W. (1984). Comprehensive Heterocyclic Chemistry, Pergamon Press.","DOI":"10.1016\/B978-0-08-030726-8.50008-7"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2897","DOI":"10.1021\/jo00818a042","article-title":"Cyclopropyl 2-pyrrolyl ketone","volume":"36","author":"Cooper","year":"1971","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1248\/cpb.44.48","article-title":"\u03b2-Acylation of ethyl pyrrole-2-carboxylate by Friedel-Crafts acylation : Scope and limitations (synthetic studies on indoles and related compounds. XXXVIII)","volume":"44","author":"Tani","year":"1996","journal-title":"Chem. Pharm. Bull."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3214","DOI":"10.1021\/jo00167a014","article-title":"Regioselective synthesis of acylpyrroles","volume":"48","author":"Kakushima","year":"1983","journal-title":"J. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"896","DOI":"10.1139\/v85-149","article-title":"Pyrrole chemistry. XXVIII. Substitution reactions of 1-(phenylsulfonyl)pyrrole and some derivatives","volume":"63","author":"Anderson","year":"1985","journal-title":"Can. J. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/15\/5\/2972\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:02:15Z","timestamp":1760220135000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/15\/5\/2972"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,4,27]]},"references-count":34,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2010,5]]}},"alternative-id":["15052972"],"URL":"https:\/\/doi.org\/10.3390\/molecules15052972","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2010,4,27]]}}}