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Journal articles on the topic 'Vilsmeier Reagenz'

Author: Grafiati

Published: 29 September 2021

Last updated: 30 July 2025

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1

Brehme, R., E. Gründemann, and M. Schneider. "Reaktion von Acetophenonmonomethyl- und -dimethylhydrazonen mit dem Vilsmeier-Reagenz; Bildung von Pyrazol-4-carbiminiumsalzen: ein Beitrag zum Mechanismus." Journal für praktische Chemie 342, no. 7 (2000): 700–706. http://dx.doi.org/10.1002/1521-3897(200009)342:7<700::aid-prac700>3.0.co;2-u.

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2

Awad, Ibrahim M. A., and Khairy M. Hassan. "Studies in Vilsmeier-Haack reaction: Reaction of 3-methyl-1-phenyl-4-arylidene-5-pyrazolone." Collection of Czechoslovak Chemical Communications 54, no. 3 (1989): 706–12. http://dx.doi.org/10.1135/cccc19890706.

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The 3-methyl group in Ia, b has been found to undergo diformylation by Vilsmeier reagent to give the aminoacrolein derivatives (IIa, b). Treatment of IIa, b with different reagents affords the related 1-phenyl-4-arylidene-5-pyrazolone derivatives with different heterocyclic systems in the 3-position. The Vilsmeier reaction on pyrazolopyrazole (XIII) have been utilized to prove chemically that new heterocyclic systems are formed only at the 3-position and no addition on the carbon-carbon double bond in the conjugated system O=C-C=C-(B) takes place.

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3

Rhee, Hakjune, Yuri Jeong, Jaeyoung Ban, and Minkyung Lim. "A Novel Synthesis of N-Sulfonylformamidines from N-Sulfonylsulfonamides." Synthesis 50, no. 09 (2018): 1867–74. http://dx.doi.org/10.1055/s-0036-1591936.

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N-Sulfonylformamidines were synthesized from N-sulfonylsulfonamides by reacting with p-toluenesulfonyl chloride (TsCl) and N,N -disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N,N-disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N-sulfonylformamidines were obtained in 60% to quantitative yields.

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4

Corbett, Michael, and Seb Caille. "A Bench-Stable Vilsmeier Reagent for in situ Alcohol Activation: Synthetic Application in the Synthesis of 2-Amino-2-Thiazolines." Synlett 28, no. 20 (2017): 2845–50. http://dx.doi.org/10.1055/s-0036-1589086.

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A robust, chemoselective direct condensation/cyclization of thioureas and amino alcohols is described. Employing a bench-stable Vilsmeier reagent, methoxymethylene-N,N-dimethyliminium methyl sulfate, the selective in situ activation of alcohols is achieved with high efficiency and broad functional-group tolerance. The reversible interaction of the Vilsmeier reagent with substrate was key to the success of this activation strategy.

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5

Lu, Shi-Han, Po-Lin Liu, and Fung Fuh Wong. "Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction." RSC Advances 5, no. 58 (2015): 47098–107. http://dx.doi.org/10.1039/c5ra07707a.

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6

Kumar, Ajay, Om Prakash, Mayank Kinger, and Shiv P. Singh. "Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier–Haack reaction — Isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles." Canadian Journal of Chemistry 84, no. 3 (2006): 438–42. http://dx.doi.org/10.1139/v06-015.

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Arylhydrazones of dehydroacetic acid (DHA) underwent Vilsmeier–Haack reaction to generate the corresponding 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles (1) with the pyrone moiety of the DHA remaining intact. However, when the reaction was performed using 1 equiv. of the reagent, compounds of 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles (2a–2f) were obtained, which underwent smooth conversion to 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles (1) on further treatment with another equivalent of the Vilsmeier–Haack reagent. This unreported

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7

Roopa, Redamala*. "UNDER SOLVENT-FREE CONDITIONS, ACETYLATION and VILSMEIER-HAACK FORMYLATION REACTIONS WITH ACETANILIDES and ANILINES." Journal of Pharma Research 11, no. 06 (2022): 72–84. https://doi.org/10.5281/zenodo.7813300.

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Abstract:  <strong>The Vilsmeier-Haack reaction with anilines and acetanilides was carried out without the use of a solvent. At room temperature, the reactants are put in a mortar and ground with a pestle for 20 to 30 minutes. Formyl derivatives were generated in surprisingly good yields when dimethyl formamide (DMF) and POCl3 were used as the VH reagent. Nevertheless, acetyl derivatives were generated when DMF was substituted for DMA in the formulation of the VH reagent. The results of solvent free reactions are better to those of solution phase reactions, with high yields and much short

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8

Ruberte, Ana Carolina, Carlos Aydillo, Arun K. Sharma, Carmen Sanmartín, and Daniel Plano. "Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis of a novel selenoindolinone with potent anticancer activity." RSC Advances 10, no. 63 (2020): 38404–8. http://dx.doi.org/10.1039/d0ra07332f.

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9

Nasuhipur, Forough, Zarrin Ghasemi, Morgane Poupon, and Michal Dušek. "POCl₃ mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles." RSC Advances 13, no. 26 (2023): 17812–16. http://dx.doi.org/10.1039/d3ra02515b.

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10

Guzmán, Angel, Moises Romero, and Joseph M. Muchowski. "Vilsmeier–Haack reaction with succinamidals. A convenient synthesis of 5-chloropyrrole-2-carboxaldehydes and 5-chloropyrrole-2,4-dicarboxaldehydes." Canadian Journal of Chemistry 68, no. 5 (1990): 791–94. http://dx.doi.org/10.1139/v90-125.

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It is shown that the reaction of N-alkylsuccinamidals (2) with the Vilsmeier–Haack reagent derived from DMF and phosphorus oxychloride can be controlled to preferentially produce either 5-chloropyrrole-2-carboxaldehydes (8) or 5-chloropyrrole-2,4-dicarboxaldehydes (9). The corresponding N-unsubstituted aldehydes are obtained when N-tert-butoxycarbonylsuccinamidal (11) is the substrate in the above reactions. Keywords: Vilsmeier–Haack reaction, succinamidals, 5-chloropyrrole-2-carboxaldehydes, 5-chloropyrrole-2,4-dicarboxaldehydes.

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11

Hartmann, Horst. "A Simple Route to Benz[a]acridinium Salts." Zeitschrift für Naturforschung B 66, no. 7 (2011): 711–14. http://dx.doi.org/10.1515/znb-2011-0711.

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12

Caroleo, Fabrizio, Greta Petrella, Lorena Di Zazzo, et al. "A Leopard Cannot Change Its Spots: Unexpected Products from the Vilsmeier Reaction on 5,10,15-Tritolylcorrole." Molecules 25, no. 16 (2020): 3583. http://dx.doi.org/10.3390/molecules25163583.

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The reaction of 5,10,15-tritolylcorrole with 3-dimethylaminoacrolein (3-DMA) and POCl3 gives a further example of the rebel reactivity of this contracted macrocycle. While no evidence was obtained for the formation of the expected β-acrolein corrole, the inner core substituted N21,N22-3-formylpropylcorrole and the 10-acrolein isocorrole were the reaction products. By increasing the temperature or the amount of the Vilsmeier reagent, the 10-isocorrole became the unique reaction product. The formation of the isocorrole by electrophilic attack of the Vilsmeier reagent to the 10-position of the co

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13

Tasneem. "Vilsmeier-Haack Reagent (Halomethyleneiminium Salt)." Synlett, no. 1 (2002): 0138–39. http://dx.doi.org/10.1055/s-2003-36241.

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14

Smetanin, N. V., S. A. Varenichenko, A. V. Kharchenko, O. K. Farat, and V. I. Markov. "Synthesis of new substituted pyridines via Vilsmeier-Haack reagent." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 1 (March 2023): 34–39. http://dx.doi.org/10.32434/0321-4095-2023-146-1-34-39.

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New substituted pyridines were synthesized by the reaction of spiroimidazolidinones with the Vilsmeier-Haack reagent (PBr3/DMF) with satisfactory yields. The reaction proceeds as an electrophilic trigger process according to the push-pull mechanism due to the anomeric effect of two nitrogen atoms with an increase in the primary heterocycle. An explanation is proposed for the different chemical behavior of 5',6',7',8'-tetrahydro-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one and spiroimidazolidinones under Vilsmeier-Haack reaction conditions. The likely reason is the hybridization of the am

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15

Chahal, Mamta, Sudeep Dhillon, Priyanka Rani, Ginna Kumari, Deepak Kumar Aneja, and Mayank Kinger. "Unravelling the synthetic and therapeutic aspects of five, six and fused heterocycles using Vilsmeier–Haack reagent." RSC Advances 13, no. 38 (2023): 26604–29. http://dx.doi.org/10.1039/d3ra04309f.

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16

Mphahlele, Malose J., and Mmakwena M. Mmonwa. "Vilsmeier–Haack reaction of 7-acetyl-2-arylindoles: a convenient method for the synthesis of 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2204–11. http://dx.doi.org/10.1039/c8ob03040e.

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17

Zhi, Peng, Zi-Wei Xi, Dan-Yan Wang, et al. "Vilsmeier–Haack reagent mediated synthetic transformations with an immobilized iridium complex photoredox catalyst." New Journal of Chemistry 43, no. 2 (2019): 709–17. http://dx.doi.org/10.1039/c8nj05288c.

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18

Bala, Renu, Vandana Devi, Pratibha Singh, et al. "Regioselective Synthesis of Potent 4,5,6,7-Tetrahydroindazole Derivatives via Microwave-assisted Vilsmeier-Haack Reaction and their Antioxidant Activity Evaluation." Letters in Organic Chemistry 16, no. 3 (2019): 194–201. http://dx.doi.org/10.2174/1570178615666180919120329.

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Background: Tetrahydroindazole, a member of the fused-pyrazole system, is a least studied class of heterocyclic compounds owing to its scarcity in nature. However, a large number of synthetically prepared tetrahydroindazoles are known to show a variety of biological activities such as interleukin- 2 inducible T-Cell kinase inhibitors, AMPA receptor positive allosteric modulators, antitumor, antituberculosis, anti-inflammatory and antimicrobial activities. Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron rich arenes. Even though Vilsmeier

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19

Kirsch, Gilbert, Ahmed Abdelwahab, and Atef Hanna. "Targeted Synthesis of 4-Chloro-3-formylthieno[2,3-b]pyridine and/or 4-Chlorothieno[2,3-b]pyridine by Reaction between N-Protected 3-Acetyl-2-aminothiophenes and Vilsmeier–Haack Reagent." Synthesis 49, no. 13 (2017): 2971–79. http://dx.doi.org/10.1055/s-0036-1588992.

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Formylated chlorothieno[2,3-b]pyridine derivatives were synthesized by reaction between N-protected 3-acetyl-2-aminothiophenes and Vilsmeier–Haack reagent under classical conditions. These products were not accessible without N-protection of the starting materials or by reaction between the reagent and 4-chlorothieno[2,3-b]pyridine under any conditions. The conditions of the reaction could be altered to produce unformylated derivatives in better yields than reaction with unprotected aminothiophene.

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20

Farat, O. K., E. V. Zaliznaya, S. A. Varenichenko, and V. I. Markov. "Rearrangement of substituted pyrimidin-4-ones under the Vilsmeier-Haack reaction." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 1 (January 2021): 101–9. http://dx.doi.org/10.32434/0321-4095-2021-134-1-101-109.

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The article describes the result of our study on rearrangements of four heterocyclic systems with variation of oxygen and nitrogen atoms, in particular, the results of formylation of 2,2-disubstituted hydroquinazolones under the conditions of the Vilsmeier-Haack reaction. A new rearrangement of spiro derivatives of quinazolin-4(3H)-ones was discovered under the action of a formylating reagent with the formation of predicted 1-cyclohex(pent)-1-en-1-ylchinazolin-4-(1H)-ones. The absence of this rearrangement for 2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one is explained. 6',7',7'-Trimethyl-1',5',

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21

Huy, Peter Helmut. "Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides." Synthesis 51, no. 12 (2019): 2474–83. http://dx.doi.org/10.1055/s-0037-1611798.

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Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N-formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.

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22

Erkin, A. V., and V. I. Krutikov. "Formylation of 6-Aminouracil with Vilsmeier Reagent." Russian Journal of General Chemistry 74, no. 1 (2004): 146–47. http://dx.doi.org/10.1023/b:rugc.0000025185.52744.8a.

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23

Yu, Xiuling, and Horst Hartmann. "Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids." Zeitschrift für Naturforschung B 69, no. 5 (2014): 501–8. http://dx.doi.org/10.5560/znb.2014-4001.

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By reaction of heterocyclic-substituted 1-azo-naphth-2-ols with the Vilsmeier reagent or with strong acids polycyclic azolo[1,2,4]triazinium salts are formed in good yields. The azolo[1,2,4] triazinium salts exhibit similar UV=Vis absorption properties as the starting azo compounds, but in contrast to those the fluorescence appears in the visible range.

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24

Mane, Ramchandra Bhimrao, and Abhijit Jaysingrao Kadam. "A New Synthesis of Occidol." Collection of Czechoslovak Chemical Communications 64, no. 3 (1999): 533–38. http://dx.doi.org/10.1135/cccc19990533.

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Sodium borohydride reduction of 5,8-dimethyl-3,4-dihydronaphthalen-1-(2H)-one (4) yielded 5,8-dimethyl-1,2,3,4-tetrahydro-1-naphthol (5). The tetralol 5 on Vilsmeier-Haack reaction with N,N-dimethylacetamide yielded 1-(5,8-dimethyl-3,4-dihydro-2-naphthyl)ethan-1-one (7) which on hydrogenation over Pd/C afforded 1-(5,8-dimethyl-1,2,3,4-tetrahydro-2-naphthyl)ethan-1-one (8). The tetralol 5 on Vilsmeier-Haack formylation gave 5,8-dimethyl-3,4-dihydro-2-naphthaldehyde (9) which on reduction with lithium aluminium hydride followed by oxidation with the Jones reagent furnished 5,8-dimethyl-1,2,3,4-t

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25

Cheng, Ying, Simon Goon, and Otto Meth-Cohn. "Carbenes from vilsmeier reagents by the action of bases in POCl3; the umpolung of vilsmeier reagents." Chemical Communications, no. 11 (1996): 1395. http://dx.doi.org/10.1039/cc9960001395.

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26

Zhu, Wu Fu, Yuan Biao Tu, Shan Xu, et al. "Rapid Synthesis of 4-oxo-4H-chromene-3-carboxylic Acid." Advanced Materials Research 1081 (December 2014): 16–19. http://dx.doi.org/10.4028/www.scientific.net/amr.1081.16.

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4-Oxo-4H-chromene-3-carboxylic acid (8) is an important intermediate in many biologically active compounds. In this work, a rapid synthetic method for compound 8 was established. The compound 8 was synthesized from the commercially available 1-(2-hydroxyphenyl) ethanone 9 through two steps including vilsmeier reaction and oxidation by Jones reagent. The structure was confirmed by1HNMR and13CNMR spectrum. Furthermore, the synthetic method was optimized.

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27

Venugopal, Murugapillai, and Paramasivam T. Perumal. "Syntheses of substituted isoxazolines using Vilsmeier-Haack reagent." Proceedings / Indian Academy of Sciences 105, no. 1 (1993): 19–23. http://dx.doi.org/10.1007/bf02841346.

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28

Tebby, John C., and Stuart E. Willetts. "Structure and Reactivity of the Vilsmeier Formylating Reagent." Phosphorous and Sulfur and the Related Elements 30, no. 1-2 (1987): 293–95. http://dx.doi.org/10.1080/03086648708080579.

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29

Wuts, Peter G. M., Jill M. Northuis, and Tricia A. Kwan. "The Synthesis of Oxazolines Using the Vilsmeier Reagent." Journal of Organic Chemistry 65, no. 26 (2000): 9223–25. http://dx.doi.org/10.1021/jo000664r.

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30

Amaresh, R. R., and P. T. Perumal. "Ring opening of chalcone epoxides with vilsmeier reagent." Tetrahedron Letters 36, no. 40 (1995): 7287–88. http://dx.doi.org/10.1016/0040-4039(95)01466-u.

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31

Om, Prakash, Kumar Ravi, Sharma Deepak, and Bhardwaj Vikas. "Behaviour of o-hydroxyacetophenones towards action of POCI3/DMF (Vilsmeier reagent) in presence of BF3.Et20 : a novel observation in the synthesis of chromones." Journal of Indian Chemical Society Vol. 81, Oct 2004 (2004): 888–90. https://doi.org/10.5281/zenodo.5832903.

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Department of Chemistry, Kurukshetra University, Kurukshetra-136 119, India <em>E-mail</em>: search@granth.kuk.ernet.in; oprakash50@ sify.com <em>Manuscript received 3 September 2003, accepted 11 May 2004</em> The influence of the presence of BF<sub>3</sub>.Et<sub>2</sub>O on the Vilsmeier reactions of <em>o</em>-hydroxyacetophenones and related naphthophenones has been examined. A significant and novel feature of this study is the development of new and facile procedure for the synthesis of some chromones. The reaction offers a first example of monoformylation of <em>o</em>-hydroxyacetophenon

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32

Cheng, Ying, Simon Goon, and Otto Meth-Cohn. "Umpoled Vilsmeier reagents. The chemistry of aminochlorocarbenes derived from Vilsmeier reagents by the action of bases 1." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1998): 1619–26. http://dx.doi.org/10.1039/a800800k.

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33

Baluja, Shipra, Nilesh Godvani, and Sumitra Chanda. "Antibacterial Screening of some Heterocyclic Compounds Containing Quinoline Nucleus." International Letters of Chemistry, Physics and Astronomy 76 (October 2017): 27–40. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.76.27.

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In this work, some novel derivatives of Cyanopyridines and Isoxazoles were synthesized using Vilsmeier-Haack reagent and their structures were confirmed by FTIR, 1H NMR and mass spectroscopic methods. The antibacterial activities of these synthesized compounds were studied in DMSO and DMF by agar well diffusion method against some Gram positive and Gram negative bacteria. It is observed that activity depends upon three S: solvent, strain and structure.

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34

Baluja, Shipra, Nilesh Godvani, and Sumitra Chanda. "Antibacterial Screening of some Heterocyclic Compounds Containing Quinoline Nucleus." International Letters of Chemistry, Physics and Astronomy 76 (October 26, 2017): 27–40. http://dx.doi.org/10.56431/p-18r86g.

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In this work, some novel derivatives of Cyanopyridines and Isoxazoles were synthesized using Vilsmeier-Haack reagent and their structures were confirmed by FTIR, 1H NMR and mass spectroscopic methods. The antibacterial activities of these synthesized compounds were studied in DMSO and DMF by agar well diffusion method against some Gram positive and Gram negative bacteria. It is observed that activity depends upon three S: solvent, strain and structure.

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35

Aneesa, F., K. C. Rajanna, Y. Arun Kumar, and M. Arifuddin. "Transition Metal Ions as Efficient Catalysts for Facile Ortho-Formylation of Phenols under Vilsmeier–Haack Conditions." Organic Chemistry International 2012 (November 19, 2012): 1–7. http://dx.doi.org/10.1155/2012/289023.

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Aromatic compounds (phenols), when treated with Vilsmeier Haack (V-H) reagent in the presence of transition metal ions such as Cu(II), Ni(II), Co(II), Cd(II), and Zn(II) under reflux conditions, afforded corresponding ortho-formyl derivatives in good yields. Under normal conditions the metal-ion-free V-H reactions are too sluggish and resulted in poor yields. This protocol provides highly regioselective formylation under a mild and efficient condition with simple workup.

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36

Noh, Eun Sun, Sung Min Kim, and Yang-Heon Song. "4-(3-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine." Molbank 2020, no. 2 (2020): M1136. http://dx.doi.org/10.3390/m1136.

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A new hybrid compound, 4-(3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine 3, with promising biological activity was efficiently synthesized by the reaction of 3-phenyl-1-(thieno[3,2-d]pyrimidin-4-yl)-1H-pyrazol-5-amine with Vilsmeier–Haack reagent and subsequent treatment with ammonium carbonate. The structure of the synthesized compound was fully characterized by 1H-, 13C-NMR, IR spectroscopy, mass-spectrometry and elemental analysis.

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37

Katritzky, Alan R., Irina V. Shcherbakova, Robert D. Tack, and Peter J. Steel. "Reactions of unactivated olefins with Vilsmeier reagents." Canadian Journal of Chemistry 70, no. 7 (1992): 2040–45. http://dx.doi.org/10.1139/v92-257.

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Reactions of N-formylmorpholine/POCl3 with several unactivated olefins yield the corresponding α,β-unsaturated aldehydes. Norbornene affords with dimethylformamide/POCl3 a product formed by a novel inverse-electron demand Diels–Alder reaction of an acyclic 2-azoniodiene. The structure of this product was confirmed by X-ray analysis. Crystals are monoclinic: a = 8.025(3), b = 11.670(3), c = 9.309(4) Å, β = 108.03(3)°, P21, Z = 2; the structure was refined to R = 0.044 for 1379 independent observed reflections.

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38

Qian, Dingquan, Xingzhong Zeng, Xiaodong Shi, Ruzhen Cao, and Lunzu Liu. "The Reactions of Hydridophosphorane with Vilsmeier Reagents." Heteroatom Chemistry 8, no. 6 (1997): 517–20. http://dx.doi.org/10.1002/(sici)1098-1071(1997)8:6<517::aid-hc10>3.0.co;2-u.

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39

CHENG, Y., S. GOON, and O. METH-COHN. "ChemInform Abstract: Umpoled Vilsmeier Reagents. The Chemistry of Aminochlorocarbenes Derived from Vilsmeier Reagents by the Action of Bases." ChemInform 29, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199837132.

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40

Kaur, Aneet Kamal, Renu Bala, Poonam Kumari, Sumit Sood, and Karan Singh. "Microwave Assisted Vilsmeier-Haack Reaction on Substituted Cyclohexanone Hydrazones: Synthesis of Novel 4,5,6,7-Tetrahydroindazole Derivatives." Letters in Organic Chemistry 16, no. 3 (2019): 170–75. http://dx.doi.org/10.2174/1570178615666180917101637.

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Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron-rich arens. Even though Vilsmeier-Haack reaction was studied on a wide variety of hydrazones of enolizable ketones, literature lacks the examples of the use of 4-substituted cyclohexanones as a substrate. The cyclization potential of hydrazones of cyclic keto compounds is still interested topic of investigation. In the present study, the reaction of various hydrazines with 4-substituted cyclohexanones was proceeded and the resulted hydrazones in crude form were treated with Vilsmeier- Haac

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41

Rajanna, K., Bhooshan Muddam, P. Venkanna, M. Venkateswarlu, and M. Satish Kumar. "Symmetrical Trichlorotriazine Derivatives as Efficient Reagents for One-Pot Synthesis of 3-Acetyl-2-chloroquinolines from Acetanilides under Vilsmeier–Haack Conditions." Synlett 29, no. 01 (2017): 85–88. http://dx.doi.org/10.1055/s-0036-1589099.

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Symmetrical trichlorotriazine derivatives such as 2,4,6-trichloro-1,3,5-triazine and trichloroisocyanuric acid were explored as Vilsmeier–Haack type reagents in the presence of N,N-dimethylacetamide for the effective synthesis of 3-acetyl-2-chloroquinolines from acetanilides. Ultrasonication led to shorter reaction times than conventional heating and gave yields comparable to those obtained under reflux conditions.

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42

Konwar, Dilip, Romesh C. Boruah, and Jagir S. Sandhu. "A novel reaction of vilsmeier reagent with 2,1-benzisoxazoles." Tetrahedron Letters 28, no. 9 (1987): 955–56. http://dx.doi.org/10.1016/s0040-4039(00)95885-4.

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Pereira de Abreu, Marluza, Adan de Carvalho Nunes, Felipe Lange Coelho, and Leandra Franciscato Campo. "Highly conjugated streptocyanine-ESIPT dyes via Vilsmeier-Haack reagent." Journal of Luminescence 213 (September 2019): 98–107. http://dx.doi.org/10.1016/j.jlumin.2019.04.063.

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44

Perumal, P. T. "ChemInform Abstract: Synthesis of Heterocyclic Compounds Using Vilsmeier Reagent." ChemInform 33, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.200223271.

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45

Chirkova, Zhanna V., Sergey I. Filimonov, and Igor G. Abramov. "SYNTHESIS OF BENZOFURAN-5,6-DICARBONITRILES ANNELATED WITH PYRAZOLE CYCLE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, no. 6 (2017): 45. http://dx.doi.org/10.6060/tcct.2017606.5576.

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The principal method for the preparation of substituted 4-formyl-1H-pyrazoles was the treatment of hydrazones of different structure with Vilsmeier-Haack reagent. However, for the heterocyclic benzofuran system this reaction is rarely used. Synthetic methods for preparation of novel substituted 3-(4-fomyl-1H-pyrazole-3-yl)-2-methylbenzofuran-5,6-dicarbonitriles and 2-(1H-pyrazole-4-yl)-benzofuran-5,6-dicarbonitriles were developed by modification of 2,3-disubstituted benzofuran-5,6-dicarbonitriles via Vilsmeier-Haack reaction. New substituted 3-(4-fomyl-1H-pyrazole-3-yl)-2-methylbenzofuran-5,6

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46

Tachrim, Zetryana Puteri, Kazuhiro Oida, Fumina Ohashi та ін. "Synthesis of TFA-protected α-Amino Acid Chloride via a Vilsmeier Reagent for Friedel–Crafts Acylation". Letters in Organic Chemistry 17, № 8 (2020): 645–53. http://dx.doi.org/10.2174/1570178617666200207111127.

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α-Amino acid chlorides are reactive coupling agents in amide (peptide) formation. The Vilsmeier reagent ((chloromethylene)dimethylammonium chloride) offers a convenient way to prepare α-amino acid chlorides for peptide synthesis. Its use with N-trifluoracetyl (TFA)-protected isoleucine and allo-isoleucine is described. The 1H-NMR of the α-proton signal offers a convenient way to monitor the chirality retention in the acid chloride forming reaction and subsequent Friedel-Crafts acylation of arenes which result in α-amino acid aryl-ketone with no loss of chirality.

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47

Tran, Vy-Phuong, Nobuyuki Matsumoto, Phattananawee Nalaoh, Haoyu Jing, Chih-Yuan Chen, and Jonathan S. Lindsey. "Dihydrooxazine Byproduct of a McMurry–Melton Reaction en Route to a Synthetic Bacteriochlorin." Organics 3, no. 3 (2022): 262–74. http://dx.doi.org/10.3390/org3030019.

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A synthetic route to gem-dimethyl-substituted bacteriochlorins—models of native bacteriochlorophylls—relies on the formation of a dihydrodipyrrin precursor via a series of established reactions: van Leusen pyrrole formation, Vilsmeier formylation, Henry reaction, borohydride reduction, Michael addition, and McMurry–Melton pyrroline formation. The latter is the least known of the series. Here, the McMurry–Melton reaction of a 2-(6-oxo-2-nitrohexyl)pyrrole in the presence of TiCl3 and an ammonium acetate buffer formed the expected Δ1-pyrroline, as well as an unexpected polar, cyclic byproduct (a

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48

Malik, Qasim M., Andrew B. Mahon, Donald C. Craig, and Andrew C. Try. "Reaction of Tröger’s base analogues with Vilsmeier reagents." Tetrahedron 67, no. 44 (2011): 8509–14. http://dx.doi.org/10.1016/j.tet.2011.08.095.

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Jarrahpour, Aliasghar, and Maaroof Zarei. "The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones." Tetrahedron 65, no. 15 (2009): 2927–34. http://dx.doi.org/10.1016/j.tet.2009.02.005.

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50

Awad, Ibrahim M. A., and Khairy M. Hassan. "Studies in Vilsmeier-Haack reaction. Application to quinoxalinones." Collection of Czechoslovak Chemical Communications 55, no. 11 (1990): 2715–21. http://dx.doi.org/10.1135/cccc19902715.

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The 3-methyl group in quinoxalinones I and II has been found to undergo diformylation by Vilsmeier reagent to give the corresponding aminoacrolein derivatives (III, IV). Condensation and/or interaction of III or IV with some secondary heterocyclic amines and/or with hydrazine, phenylhydrazine and hydroxylamine affords the related 3-methyl-N-(1H)-2-quinoxalinone and 1,3-dimethyl-2-quinoxalinone derivatives (VII-XVIII), some with pronounced fluorescence activities. All synthesized compounds have been screened in vitro for their antimicrobial activities against Gram-positive and Gram-negative bac

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