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Journal articles on the topic 'N-acylpyrroles'

Author: Grafiati

Published: 20 February 2023

Last updated: 31 July 2025

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1

Duan, Jian-Hua, Rui-Jie Mi, Jing Sun, and Ming-Dong Zhou. "Regioselective C5 alkenylation of 2-acylpyrroles via Pd(ii)-catalyzed C–H bond activation." Organic Chemistry Frontiers 5, no. 2 (2018): 162–65. http://dx.doi.org/10.1039/c7qo00732a.

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2

Goldys, Anna M., and Christopher S. P. McErlean. "N-Acylpyrroles: More Than Amides." European Journal of Organic Chemistry 2012, no. 10 (2011): 1877–88. http://dx.doi.org/10.1002/ejoc.201101470.

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3

Chen, Weiqiang, Yin-Lin Zhang, Hui-Jing Li, Xiang Nan, Ying Liu, and Yan-Chao Wu. "Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction." Synthesis 51, no. 19 (2019): 3651–66. http://dx.doi.org/10.1055/s-0039-1690002.

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N-Sulfonyl- and N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide oxidants. This protocol possesses many advantages, such as using a nonhazardous oxidant and readily available starting materials, operating in one pot, and showing a broad sub

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4

Goldys, Anna M., and Christopher S. P. McErlean. "ChemInform Abstract: N-Acylpyrroles: More Than Amides." ChemInform 43, no. 30 (2012): no. http://dx.doi.org/10.1002/chin.201230235.

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5

D’Silva, Claudius, and Rifat Iqbal. "A New Method to N-Arylmethylenepyrroles from N-Acylpyrroles." Synthesis 1996, no. 04 (1996): 457–58. http://dx.doi.org/10.1055/s-1996-4247.

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6

Cui, Hai-Lei, and Fujie Tanaka. "One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis." Org. Biomol. Chem. 12, no. 31 (2014): 5822–26. http://dx.doi.org/10.1039/c4ob01019a.

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Polysubstituted 3-acylpyrroles were synthesized from readily available unsaturated ketones and N-substituted propargylated amines via an aza-Michael/alkyne carbocyclization cascade followed by oxidation in one pot.

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7

D'SILVA, C., and R. IQBAL. "ChemInform Abstract: A New Method to N-Arylmethylenepyrroles from N-Acylpyrroles." ChemInform 27, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199636112.

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8

X., J. Shi, K. Su W., and G. Shan W. "Vilsmeier-Haack preparation of 2-acylpyrroles using bis( trichloromethyl)carbonate and N,N -dimethylacylamines." Journal of Indian Chemical Society Vol. 82, Nov 2005 (2005): 1019–21. https://doi.org/10.5281/zenodo.5825042.

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College of Pharmaceutical Sciences, Zhejiang University of Technology. Hangzhou, 310014, P. R. China <em>E-mail</em>: suweike@zjut.edu.cn                     <em>Fax</em> : 86-571-88320752 <em>Manuscript received 14 February 2005, revised 28 May 2005, accepted 18 July 2005</em> A series of 2-acylpyrroles were synthesized by using bis(trichloromethyl)carbonate and <em>N,N</em>-dimethylacylamines as Vilsmeier-Haack reagents under mild conditions in good yields.

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9

Brandänge, Svante, Benito Rodriguez, Nils Gunnar Johansson, and Ann-Britt Wassgren. "N-Acylpyrroles as Acylating Agents. Synthesis of beta-Keto Esters." Acta Chemica Scandinavica 41b (1987): 740–44. http://dx.doi.org/10.3891/acta.chem.scand.41b-0740.

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10

Yang, Fan, Dong Zou, Shuguang Chen, et al. "Transition Metal‐Free Aroylation of Diarylmethanes with N ‐Bn‐ N ‐Boc Arylamides and N ‐Acylpyrroles." Advanced Synthesis & Catalysis 362, no. 16 (2020): 3423–30. http://dx.doi.org/10.1002/adsc.202000622.

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11

Evans, David A., George Borg, and Karl A. Scheidt. "Remarkably Stable Tetrahedral Intermediates: Carbinols from Nucleophilic Additions to N-Acylpyrroles." ChemInform 34, no. 1 (2003): no. http://dx.doi.org/10.1002/chin.200301107.

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12

Du, Dan, та Wei-Liang Duan. "Palladium-catalyzed 1,4-addition of diarylphosphines to α,β-unsaturated N-acylpyrroles". Chemical Communications 47, № 39 (2011): 11101. http://dx.doi.org/10.1039/c1cc13785a.

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13

Kämpfe, Alexander, Erica Brendler, Edwin Kroke, and Jörg Wagler. "2-Acylpyrroles as Mono-anionicO,N-Chelating Ligands in Silicon Coordination Chemistry." Chemistry - A European Journal 20, no. 30 (2014): 9409–18. http://dx.doi.org/10.1002/chem.201402803.

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14

Castoldi, Laura, Wolfgang Holzer, Thierry Langer, and Vittorio Pace. "Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles." Chemical Communications 53, no. 68 (2017): 9498–501. http://dx.doi.org/10.1039/c7cc05215d.

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15

Anderson, Hugh J., Charles E. Loader, Ru Xun Xu, et al. "Pyrrole chemistry. XXVIII. Substitution reactions of 1-(phenylsulfonyl)pyrrole and some derivatives." Canadian Journal of Chemistry 63, no. 4 (1985): 896–902. http://dx.doi.org/10.1139/v85-149.

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The preparative value of the 1-(phenylsulfonyl) N-blocking and directing group for the synthesis of 3-acylpyrroles has been further evaluated. Acetylation and benzoylation are strongly regiospecific and give good yields. However, the regiospecificity is not general and other substitution reactions give mixtures of 2- and 3-substitution or even mostly 2-substitution. Friedel and Crafts tert-butylation gives 3-tert-butyl-1-(phenylsulfonyl)pyrrole and provides a useful route to tert-butylpyrrole, but ethylation and isopropylation give mixtures. Acylations of 2- and 3-alkyl-1-(phenylsulfonyl)pyrro

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16

Pichon, Delphine, Jennifer Morvan, Christophe Crévisy, and Marc Mauduit. "Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors." Beilstein Journal of Organic Chemistry 16 (February 17, 2020): 212–32. http://dx.doi.org/10.3762/bjoc.16.24.

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The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic

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17

Maehara, Tomoaki, Rentaro Kanno, Satoshi Yokoshima, and Tohru Fukuyama. "A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine." Organic Letters 14, no. 7 (2012): 1946–48. http://dx.doi.org/10.1021/ol3005613.

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18

Qian, Jinyi, Wendi Shao, Qi Gao, Jiuling Li, Baomin Fan та Yafei Guo. "Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles". Tetrahedron 168 (грудень 2024): 134331. http://dx.doi.org/10.1016/j.tet.2024.134331.

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19

Brandänge, Svante, Erik Holmgren, Hans Leijonmarck, and Benito Rodriguez. "On the Preparation of N-Acylpyrroles and their Use in the Synthesis of Ketones." Acta Chemica Scandinavica 49 (1995): 922–28. http://dx.doi.org/10.3891/acta.chem.scand.49-0922.

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20

Du, Dan, та Wei-Liang Duan. "ChemInform Abstract: Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated N-Acylpyrroles." ChemInform 43, № 7 (2012): no. http://dx.doi.org/10.1002/chin.201207184.

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21

BRANDAENGE, S., E. HOLMGREN, H. LEIJONMARCK, and B. RODRIGUEZ. "ChemInform Abstract: Preparation of N-Acylpyrroles and Their Use in the Synthesis of Ketones." ChemInform 27, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199615135.

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22

Meng, Guangrong, Roman Szostak, and Michal Szostak. "Suzuki–Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N–C Cleavage." Organic Letters 19, no. 13 (2017): 3596–99. http://dx.doi.org/10.1021/acs.orglett.7b01575.

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23

Maehara, Tomoaki, Rentaro Kanno, Satoshi Yokoshima, and Tohru Fukuyama. "ChemInform Abstract: A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine." ChemInform 43, no. 31 (2012): no. http://dx.doi.org/10.1002/chin.201231104.

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24

Matsunaga, Shigeki, Hongbo Qin, Mari Sugita та ін. "Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors". Tetrahedron 62, № 28 (2006): 6630–39. http://dx.doi.org/10.1016/j.tet.2005.12.074.

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25

Uraguchi, Daisuke, Ken Yoshioka, Yusuke Ueki, and Takashi Ooi. "Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles." Journal of the American Chemical Society 134, no. 47 (2012): 19370–73. http://dx.doi.org/10.1021/ja310209g.

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26

Sakaguchi, Yusuke, Nobuhito Kurono, Kohei Yamauchi та Takeshi Ohkuma. "Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles with the Ru(phgly)2(binap)–CH3OLi Catalyst System". Organic Letters 16, № 3 (2014): 808–11. http://dx.doi.org/10.1021/ol403545b.

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27

Yamanaka, Masahiro, Ken Sakata, Ken Yoshioka, Daisuke Uraguchi, and Takashi Ooi. "Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study." Journal of Organic Chemistry 82, no. 1 (2016): 541–48. http://dx.doi.org/10.1021/acs.joc.6b02572.

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28

Uraguchi, Daisuke, Ken Yoshioka, Yusuke Ueki, and Takashi Ooi. "ChemInform Abstract: Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles." ChemInform 44, no. 17 (2013): no. http://dx.doi.org/10.1002/chin.201317024.

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29

Sakaguchi, Yusuke, Nobuhito Kurono, Kohei Yamauchi та Takeshi Ohkuma. "ChemInform Abstract: Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles with the Ru(phgly)2(binap)-CH3OLi Catalyst System." ChemInform 45, № 29 (2014): no. http://dx.doi.org/10.1002/chin.201429063.

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30

Park, So-Young, Hiroyuki Morimoto, Shigeki Matsunaga та Masakatsu Shibasaki. "Catalytic asymmetric Michael reactions of dibenzyl malonate to α,β-unsaturated N-acylpyrroles using a La(O-iPr)3/Ph-linked-BINOL complex". Tetrahedron Letters 48, № 16 (2007): 2815–18. http://dx.doi.org/10.1016/j.tetlet.2007.02.112.

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31

Zhao, Depeng, Lijuan Mao, Yuan Wang, Dongxu Yang, Quanliang Zhang та Rui Wang. "ChemInform Abstract: Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated N-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines." ChemInform 41, № 36 (2010): no. http://dx.doi.org/10.1002/chin.201036179.

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32

Gupta, Akhilesh K., R. T. Chakrasali, H. Ila, and H. Junjappa. "Reaction of Polarized KeteneS,N-Acetals with Bromoacetaldehyde Diethyl Acetal: Synthesis of 1-Substituted 3-Acyl- and 3-Nitro-2-methylthiopyrroles and 1,2-Annulated 3-Acylpyrroles." Synthesis 1989, no. 02 (1989): 141–42. http://dx.doi.org/10.1055/s-1989-27179.

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33

Huang, Pei-Qiang, and Hang Chen. "Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents." Chemical Communications 53, no. 93 (2017): 12584–87. http://dx.doi.org/10.1039/c7cc07457c.

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34

Abell, AD, and JC Litten. "Synthesis and Amino Acid Chain Extension of 1-Acylated Hydroxymethylpyrroles." Australian Journal of Chemistry 46, no. 10 (1993): 1473. http://dx.doi.org/10.1071/ch9931473.

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Acylation of pyrrole-2-carbaldehyde (3) with an N-phthaloyl amino acid chloride, N,N-diisopropylethylamine and 4-dimethylaminopyridine (dmap) gave the 1-acylpyrrole-2-carbalde-hydes (4a-c). The 1-acylated pyrroles (4d-i), (8) and (9) were similarly prepared in good yields from the relevant pyrrole derivative using dmap and either an acid chloride/N,N- diisopropylethylamine or an anhydride/triethylamine. Reduction of (4a-f) with zinc borohydride gave the 1-acylated hydroxymethylpyrroles (5a-f). A coupling of (5a) with N-Cbz-L-Val-L-Val-OH under Mitsunobu conditions gave the tetrapeptide analogu

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35

Weber, Horst, and Thomas Rohn. "Synthese und Photoisomerisierung von sterisch gehinderten 2,6-Dialkylpyridin-N-oxiden / Synthesis and Photoisomerization of Sterically Hindered 2,6-Dialkylpyridine-N-oxides." Zeitschrift für Naturforschung B 45, no. 5 (1990): 701–6. http://dx.doi.org/10.1515/znb-1990-0519.

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Synthesis of the new sterically hindered pyridine-1-oxides 2c and 6a–c is described. Copper(II)-catalyzed photolysis of 2 and 6a in aqueous medium provides only small amounts of 2-acylpyrroles 8 and 10a together with by-products. Exclusive formation and better yields of 10 can be received upon irradiation of 6 in none protic solvents at low temperature. Introduction of bulky substituents as in 6 failed to stabilize any of the postulated intermediates in order to be identified during photoreaction. It is assumed that the high rate of polymerization is caused by unstable 1,3-oxazepines like 13.

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36

Law, Katherine R., та Christopher S. P. McErlean. "Samarium-mediated intramolecular cross-couplings of an α,β-unsaturated N-acylpyrrole". Tetrahedron Letters 57, № 29 (2016): 3113–16. http://dx.doi.org/10.1016/j.tetlet.2016.06.010.

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37

Chen, Hang, Dong-Huang Chen, and Pei-Qiang Huang. "Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions." Science China Chemistry 63, no. 3 (2020): 370–76. http://dx.doi.org/10.1007/s11426-019-9665-5.

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38

Tafel, Kelley A., and Dallas K. Bates. "Intramolecular capture of Pummerer rearrangement intermediates. IV. Preparation of pyrrolo[2,1-b][1,3]benzothiazin-9-ones via intramolecular sulfenylation of an N-acylpyrrole." Journal of Organic Chemistry 57, no. 13 (1992): 3676–80. http://dx.doi.org/10.1021/jo00039a030.

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39

TAFEL, K. A., and D. K. BATES. "ChemInform Abstract: Intramolecular Capture of Pummerer Rearrangement Intermediates. Part 4. Preparation of Pyrrolo(2,1-b)(1,3)benzothiazin-9-ones via Intramolecular Sulfenylation of an N-Acylpyrrole." ChemInform 23, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199247086.

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40

Malins, Lara R., and Yutong Lin. "Synthesis of Peptide N-Acylpyrroles via Anodically Generated N,O-Acetals." Synthesis, May 9, 2022. http://dx.doi.org/10.1055/s-0041-1737411.

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AbstractAn electrochemical approach to peptide C-terminal N-acylpyrroles is described from readily accessible C-terminal hydroxyproline-containing peptides, prepared via standard Fmoc solid-phase peptide synthesis (Fmoc-SPPS). Following electrochemical decarboxylation, the reactive hydroxyproline-derived N,O-acetal intermediate is aromatized under mild acidic conditions, which enable concomitant deprotection of amino acid side-chain protecting groups. The resulting peptide N-acylpyrrole is amenable to late-stage peptide modifications, including reduction with NaBH4 to deliver a valuable C-term

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41

Dubis, Alina T., Piotr Stasiewicz, Katarzyna Pogorzelec‐Glaser, and Andrzej Łapiński. "Can 2‐acylpyrroles form an intramolecular hydrogen bond?" July 6, 2015. https://doi.org/10.1002/poc.3468.

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The formation of intramolecular hydrogen bonding by certain N‐substituted 2‐acylpyrroles has been demonstrated by B3LYP/aug‐cc‐pVDZ calculations, the quantum theory of atoms in molecules, and the natural bond orbital method.Total electron energy densities HBCP at the bond critical point of the H⋯O bond were applied to analyze the strength of these interactions. The relations between quantum theory of atoms in molecules, carbonyl stretching vibrational modes νC = O, and natural bond orbital parameters associated with the formation of the C–H⋯O interaction have been established. The short contac

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42

li, jie, Jaiqi Yao, Dong Zou, Lingfeng Chen, Patrick Walsh, and Guang Liang. "Chemoselective acylation of N-acylglutarimides with N-acylpyrroles and aryl esters under transition-metal-free conditions." Organic Chemistry Frontiers, 2021. http://dx.doi.org/10.1039/d1qo00992c.

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The imide moiety is a well-known structural motif in bioactive compounds and a useful building block in a variety of processes. Using N-acylglutarimides with MN(SiMe3)2 and either N-acylpyrroles or aryl...

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43

Epstein, Oleg L., Jung Min Seo, Nikolai Masalov, and Jin Kun Cha. "Titanium-Mediated Alkylative Coupling of N-Acylpyrroles." ChemInform 36, no. 42 (2005). http://dx.doi.org/10.1002/chin.200542128.

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44

"Suzuki–Miyaura Cross-Coupling of N-Acylpyrroles and -Pyrazoles." Synfacts 13, no. 09 (2017): 0969. http://dx.doi.org/10.1055/s-0036-1591147.

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45

"Addition of Halolithium Carbenoids to Weinreb Amides and N-Acylpyrroles." Synfacts 13, no. 11 (2017): 1185. http://dx.doi.org/10.1055/s-0036-1591350.

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46

Ekkati, Anil R., and Dallas K. Bates. "A Convenient Synthesis of N-Acylpyrroles from Primary Aromatic Amides." ChemInform 35, no. 6 (2004). http://dx.doi.org/10.1002/chin.200406099.

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47

Shi, X. J., W. K. Su, and W. G. Shan. "Vilsmeier—Haack Preparation of 2-Acylpyrroles Using Bis(trichloromethyl)carbonate and N,N-Dimethylacylamines." ChemInform 37, no. 22 (2006). http://dx.doi.org/10.1002/chin.200622113.

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48

Mita, Tsuyoshi, Kazuki Sasaki, Motomu Kanai та Masakatsu Shibasaki. "Catalytic Enantioselective Conjugate Addition of Cyanide to α,β-Unsaturated N-Acylpyrroles." ChemInform 36, № 23 (2005). http://dx.doi.org/10.1002/chin.200523111.

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49

BRANDAENGE, S., та B. RODRIGUEZ. "ChemInform Abstract: N-Acylpyrroles as Acylating Agents. Synthesis of β-Keto Esters." ChemInform 19, № 16 (1988). http://dx.doi.org/10.1002/chin.198816128.

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50

Yuan, Xiyuan, Xiaobing Xu, Xiaobo Zhou, Jiwei Yuan, Lugen Mai, and Yanzhong Li. "Copper-Catalyzed Double N-Alkenylation of Amides: An Efficient Synthesis of Di- or Trisubstituted N-Acylpyrroles." ChemInform 38, no. 27 (2007). http://dx.doi.org/10.1002/chin.200727093.

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