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Journal articles on the topic 'Dimethyl acetylenedicarboxylate'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Han, Ying, Chao-Guo Yan, Chang-Zhou Liu, Yuan-Yuan Zhang, and Jing Sun. "Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones." Synthesis 50, no. 18 (2018): 3715–22. http://dx.doi.org/10.1055/s-0037-1610438.

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The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.

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2

Anary-Abbasinejad, Mohammad, Hossein Anaraki-Ardakani, Alimohammad Dehghan, Alireza Hassanabadi, and Mohammad Reza Seyedmir. "A One-Pot Synthesis of Functionalised 3-pyrolin-2-ones by a four-component reaction between Triphenylphosphine, Primary Amines, Dimethyl Acetylenedicarboxylate and Ethyl Chlorooxoacetate." Journal of Chemical Research 2007, no. 10 (2007): 574–76. http://dx.doi.org/10.3184/030823407x255542.

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Reaction between triphenylphosphine, dimethy acetylenedicarboxylate and amines produces phosphorus ylids which undergo a smooth reaction with ethyl chlorooxoacetate and triethylamine to produce dimethyl N-aryl-(or alkyl)-4-ethoxy-5-oxo-2,5-dihydro-1 H-pyrole-2,3-dicarboxylates in high yields.

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3

Anary-Abbasinejad, Mohammad, Mohammad H. Mosslemin, Alireza Hassanabadi, and Alimohammad Dehghan. "Synthesis of Functionalised Phosphonates or Phosphoranes by Reaction between Trialkyl Phosphites or Triphenylphosphine, Dimethyl Acetylenedicarboxylate and Aldehyde Ethyl Carbazones." Journal of Chemical Research 2009, no. 5 (2009): 329–32. http://dx.doi.org/10.3184/030823409x447709.

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Protonation of the reactive intermediate produced from the reaction between trialkyl phosphites and dimethyl acetylenedicarboxylate by ethyl carbazones of aromatic aldehydes following by conjugate addition of the anion of ethyl carbazone on the phosphonium salt intermediate leads to functionalised phosphonates in good yields. Triphenylphosphine also reacted with dimethyl acetylenedicarboxylate and ethyl carbazones to produce functionalised phosphoranes in good yields.

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4

Lin, Qinghong, Djamal Djaidi, Roger Bishop, Donald C. Craig, and Marcia L. Scudder. "Ritter Reactions. XIII Reactivity of Methyl Schiff Bases with Dimethyl Acetylenedicarboxylate and Mercaptoacetic Acid." Australian Journal of Chemistry 51, no. 9 (1998): 799. http://dx.doi.org/10.1071/c98025.

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Reactions of several methyl imines with dimethyl acetylenedicarboxylate and with mercaptoacetic acid have been studied to investigate further the capricious behaviour of this functionality. The 1 : 1 adduct of imine (1) and dimethyl acetylenedicarboxylate is confirmed as the pyrroloisoquinoline structure (7) by X-ray methods [C17H17NO5, P -1, a 9·037(2), b 9·276(2), c 10·033(2) Å, α 81·99(1), β 81·28(1), γ 64·9(2)°, Z 2, R 0·044]. New products from (2) and dimethyl acetylenedicarboxylate, the 1 : 1 adduct (10) which is readily converted into the known product (9), and the 1 : 2 adduct (12), ar

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5

Dmowski, Wojciech, and Albert Biernacki. "Electrochemical trifluoromethylation of dimethyl acetylenedicarboxylate." Journal of Fluorine Chemistry 78, no. 2 (1996): 193–94. http://dx.doi.org/10.1016/0022-1139(96)03443-4.

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6

Vo, Timothy H., Rafał Korlacki, and Alexander Sinitskii. "Cis–trans isomerization of dimethyl 2,3-dibromofumarate." RSC Advances 12, no. 50 (2022): 32471–74. http://dx.doi.org/10.1039/d2ra05996g.

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The bromination of dimethyl acetylenedicarboxylate initially results in mostly trans dimethyl 2,3-dibromofumarate, which then converts into the more stable cis isomer. The trans-to-cis conversion is spontaneous and greatly accelerated by light.

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7

Schwan, Adrian L., та John Warkentin. "Reactions of 4-tert-butyl-5-methylene-3,3-dimethyl-Δ1-1,2,4-triazoline with dimethyl acetylenedicarboxylate". Canadian Journal of Chemistry 65, № 6 (1987): 1200–1204. http://dx.doi.org/10.1139/v87-201.

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4-tert-Butyl-5-methylene-3,3-dimethyl-Δ1-1,2,4-triazoline (1) reacts rapidly with dimethyl acetylenedicarboxylate (2) to afford dienamines 3 and 4 from Michael addition and enamine 5 by extensive skeletal rearrangement. Assignments of their structures and probable mechanisms of their formation are discussed.

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8

Lim, Suk Hyun, Hannara Jang, and Dae Won Cho. "Fullerene C60 promoted photochemical hydroamination reactions of an electron deficient alkyne with trimethylsilyl group containing tertiary N-alkylbenzylamines." RSC Advances 11, no. 11 (2021): 5914–22. http://dx.doi.org/10.1039/d1ra00166c.

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9

Yap, Jeanette See Leng, Bin Bin Li, Jonathan Wong, Yongxin Li, Sumod A. Pullarkat, and Pak-Hing Leung. "Development of a novel chiral palladacycle and its application in asymmetric hydrophosphination reaction." Dalton Trans. 43, no. 15 (2014): 5777–84. http://dx.doi.org/10.1039/c4dt00062e.

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10

Matsumoto, Kiyoshi, Yukio Ikemi, Motoo Shiro, Takane Uchida, and James William Lown. "Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate: regioselective formation of 1:2 Michael type adducts." Canadian Journal of Chemistry 71, no. 4 (1993): 529–33. http://dx.doi.org/10.1139/v93-075.

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Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate afforded the 1:2 adducts regioselectively and, unexpectedly, in a Michael fashion rather than in a 1,3-dipolar manner. The structure of the products was established by X-ray crystallography. Regiospecific formation of the observed product 3 can be explained by the higher nucleophilicity of the nitrogen at the 2 position than at the 3 position of the 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizine 1 owing to the contribution of a resonance structure 5 to the hybrid. This favors two successive Mich

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11

Hajinasiri, Rahimeh, and Halimeh Khatoon Khajavi. "Reaction of N-Methylimidazole and Dimethyl Acetylenedicarboxylate in the Presence of N-Phenyl Carbamate under Solvent-free Conditions." Zeitschrift für Naturforschung B 69, no. 4 (2014): 439–43. http://dx.doi.org/10.5560/znb.2014-3318.

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An efficient synthesis of 1,2,3-functionalized imidazoles and dimethyl-2-[(alkoxycarbonyl)- anilino]-2-butenedioate derivatives via one-pot reactions between N-methylimidazole, dimethyl acetylenedicarboxylate and N-phenylcarbamates under solvent-free conditions is described. The mild reaction conditions and good yields exhibit the synthetic advantage of this method.

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12

Belguedj, Roumaissa, Abdelmalek Bouraiou, Sofiane Bouacida, Hocine Merazig, and Aissa Chibani. "Pyridinium ylides in the one-pot synthesis of a new quinoline/indolizine hybrid." Zeitschrift für Naturforschung B 70, no. 12 (2015): 885–87. http://dx.doi.org/10.1515/znb-2015-0118.

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AbstractThe reaction of 1-(quinolin-2-ylmethyl)pyridinium ylide with dimethyl acetylenedicarboxylate was investigated. The X-ray crystallographic characterization of the new dimethyl 3-(quinolin-2-yl)indolizine-1,2-dicarboxylate (2) shows the formation of a five-membered ring between the pyridine ring and the methylene group.

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13

Tominaga, Yoshinori, and Kazuo Ueda. "Synthesis of dimethyl heterocyclic-o-dicarboxylates using dimethyl acetylenedicarboxylate." Journal of Heterocyclic Chemistry 42, no. 3 (2005): 337–52. http://dx.doi.org/10.1002/jhet.5570420301.

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14

Aly, Ashraf A., and Kamal M. El-Shaieb. "Reaction of N-imidoylthioureas with Dimethyl Acetylenedicarboxylate: Synthesis of new 1,3,5-thiadiazepines." Journal of Chemical Research 2007, no. 10 (2007): 563–65. http://dx.doi.org/10.3184/030823407x255579.

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15

Kurian, Jais, and Muraleedharan Kannoth M. "Synthesis of new cyclazines and 4,5-diaryl-1H-pyrrol-3(2H)-one units in discoipyrroles from indolizinone-DMAD cycloadducts." Organic & Biomolecular Chemistry 17, no. 39 (2019): 8832–48. http://dx.doi.org/10.1039/c9ob01655d.

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16

Fu, Haigen, Sabry H. H. Younes, Mohammad Saifuddin, et al. "Rapid chemoenzymatic route to glutamate transporter inhibitorl-TFB-TBOA and related amino acids." Organic & Biomolecular Chemistry 15, no. 11 (2017): 2341–44. http://dx.doi.org/10.1039/c7ob00305f.

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17

Lim, Suk Hyun, Amol B. Atar, Gunoh Bae, Kyung-Ryang Wee та Dae Won Cho. "Photoaddition reactions of N-benzylglycinates containing α-trimethylsilyl group with dimethyl acetylenedicarboxylate: competitive formation of pyrroles vs. β-enamino esters". RSC Advances 9, № 10 (2019): 5639–48. http://dx.doi.org/10.1039/c8ra09996k.

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A study was conducted to gain insight into the preparative potential of photosensitized reactions of acyclic N-benzylglycinates containing an α-trimethylsilyl group with dimethyl acetylenedicarboxylate (DMAD).

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18

Stoermer, MJ, and DP Fairlie. "A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate." Australian Journal of Chemistry 48, no. 3 (1995): 677. http://dx.doi.org/10.1071/ch9950677.

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Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution. The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids. Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol. Although not stereoselective, both fumarate and maleate aryloxy

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19

Zujewska, T., and B. Bachowska. "Benzonaphthyridine N-Oxides as 1,3-Dipoles." Australian Journal of Chemistry 49, no. 4 (1996): 523. http://dx.doi.org/10.1071/ch9960523.

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Benzonaphthyridine N-oxides give N-ylides with dimethyl acetylenedicarboxylate at room temperature, most probably by 1,3-dipolar cycloaddition followed by ring contraction to form an aziridine derivative, and ring opening.

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20

Wang, Long, Jun Li, Dongsheng Deng, et al. "Carbon–carbon bond forming reactions of acetylenic esters and ketones within frustrated phosphane/borane Lewis pair frameworks." Dalton Transactions 48, no. 31 (2019): 11921–26. http://dx.doi.org/10.1039/c9dt02624j.

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The three-component reactions of bulky diarylbutenylphosphanes with dimethyl acetylenedicarboxylate and the strong boron Lewis acid B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> give the ylide-substituted cyclopropane derivatives.

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21

Anary-Abbasinejad, Mohammad, and Alireza Hassanabadi. "Stereoselective One-Pot Synthesis of Functionalised Phosphonates by three-component reaction between Trialkyl(aryl) Phosphites, Dimethyl Acetylenedicarboxylate and indan-1,3-dione or N,N′-dimethylbarbituric acid." Journal of Chemical Research 2007, no. 8 (2007): 475–78. http://dx.doi.org/10.3184/030823407x237867.

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Protonation of the reactive intermediate produced in the reaction between trialkyl(aryl) phosphites and dimethyl acetylenedicarboxylate by CH- acids such as indane-1,3-dione and N,N′-dimethylbarbituric acid leads to functionalised phosphonates in good yields.

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22

Miftyakhova, A. R., M. B. Sidakov, T. N. Borisova, et al. "Three-Component Synthesis of New C3-Substituted 5,6-Dihydropyrrolo[2,1-a]isoquinolines." Russian Journal of Organic Chemistry 59, no. 9 (2023): 1473–81. http://dx.doi.org/10.1134/s1070428023090038.

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Abstract New C3-substituted 5,6-dihydropyrrolo[2,1-a]isoquinolines have been synthesized via three-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines, dimethyl acetylenedicarboxylate, and CH acids in anhydrous acetonitrile under microwave irradiation at 130°C.

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23

Kakehi, Akikazu, Suketaka Ito, Fumihito Ishida, and Yoshinori Tominaga. "Reaction of 1-Pyridiniothiobenzoylaminides with Dimethyl Acetylenedicarboxylate." HETEROCYCLES 41, no. 12 (1995): 2657. http://dx.doi.org/10.3987/com-95-7275.

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24

Thirmal Rao, Errabelli, Eligeti Rajanarendar, and Ananthula Krishnamurthy. "Reactions of Cinnamylideneamino Isoxazoles with Dimethyl Acetylenedicarboxylate." Bulletin of the Chemical Society of Japan 63, no. 6 (1990): 1851–53. http://dx.doi.org/10.1246/bcsj.63.1851.

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25

Ruder, Suzanne M. "Reaction of Ketophosphonium Ylides with Dimethyl Acetylenedicarboxylate." Phosphorus, Sulfur, and Silicon and the Related Elements 90, no. 1-4 (1994): 53–57. http://dx.doi.org/10.1080/10426509408016386.

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26

L'abbé, Gerrit, Jean-Paul Dekerk, and Peter van Stappen. "Addition of Hydrazoic Acid to Dimethyl Acetylenedicarboxylate." Bulletin des Sociétés Chimiques Belges 90, no. 10 (2010): 1073–74. http://dx.doi.org/10.1002/bscb.19810901012.

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27

DMOWSKI, W., and A. BIERNACKI. "ChemInform Abstract: Electrochemical Trifluoromethylation of Dimethyl Acetylenedicarboxylate." ChemInform 27, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199649102.

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28

Huang, Ying, Yi-Xin Huang, Jing Sun, and Chao-Guo Yan. "A [3+2] cycloaddition reaction for the synthesis of spiro[indoline-3,3′-pyrrolidines] and evaluation of cytotoxicity towards cancer cells." New Journal of Chemistry 43, no. 23 (2019): 8903–10. http://dx.doi.org/10.1039/c9nj00994a.

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A new type of azomethine ylides, which was in situ generated by the reaction of ethyl glycinate hydrochloride and dimethyl acetylenedicarboxylate, reacted with 3-phenacylideneoxindoline-2-ones in ethanol to give polysubstituted spiro[indoline-3,3′-pyrrolidines] in good yields.

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29

Emtiazi, Hamideh, and Mohammad Ali Amrollahi. "An Efficient Isocyanide-Based Three-Component Synthesis of Novel Ketenimines." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 3 (2014): 2363–68. http://dx.doi.org/10.24297/jac.v10i3.2286.

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This study provides a description of an efficient and simple procedure for the synthesis of dimethyl 2-(9-aryl)-3,3,6,6-tetramethyl-1,8-diox-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-3-((cyclohexylimino)methylene)succinate via a one-pot three-component reaction of cyclohexyl isocyanide, dimethyl acetylenedicarboxylate and hexahydroacridine-1,8(2H,5H)-dionesin CH2Cl2 at room temperature. Short reaction times, good to high yields and the novelty are the remarkable advantages of this work.

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30

Pearson, JR, and QN Porter. "Vinylindenes and Some Heteroanalogs in the Diels-Alder Reaction. X. Dibenzofurans From 3-Vinylbenzofurans." Australian Journal of Chemistry 44, no. 8 (1991): 1085. http://dx.doi.org/10.1071/ch9911085.

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3-Vinylbenzofuran, 3-isopropenylbenzofuran and 2-methyl-3-vinylbenzofuran give normal [4π+2π] adducts with ethenetetracarbonitrile, accompanied, in the case of the last named diene, by the isomeric cyclobutane. Normal adducts also result from these dienes and 4-phenyl-1,2,4-triazoline-3,5-dione, and from 3-vinylbenzofuran and both maleic anhydride and N- phenylmaleimide. 3-Vinylbenzofuran gives the rearranged adduct dimethyl 1,2-dihydrodibenzofuran-3,4-dicarboxylate with dimethyl acetylenedicarboxylate.

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31

Anh, Le Tuan, Truong Hong Hieu, Anatoly T. Soldatenkov, Nadezhda M. Kolyadina, and Victor N. Khrustalev. "Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1588—o1589. http://dx.doi.org/10.1107/s1600536812018867.

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The title compound, C29H33NO8, is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96 (5)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H...O hydrogen bonds.

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32

Hassan, Alaa A., Kamal M. A. El-Shaieb, Amal S. Abd El-Aal, Stefan Bräse та Martin Nieger. "Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives". Zeitschrift für Naturforschung B 70, № 4 (2015): 243–48. http://dx.doi.org/10.1515/znb-2014-0226.

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AbstractA new series of (2Z,2′E)-dimethyl 2,2′-[(2Z,2′Z)-3,3′-(alkanediyl)bis(4-oxo-2-iminothiozolidin-3-yl-5-ylidene)]acetates has been synthesized by the reaction of N,N″-(1,ω-alkanediyl)bis(N′-organylthiourea) derivatives with dimethyl acetylenedicarboxylate. The structures were established by spectroscopic data, elemental analyses, and single crystal X-ray crystallography. A rationale for the formation of the products is presented.

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33

Kysil, Andriy I., Zoia V. Voitenko, and Jean-Gérard Wolf. "Synthesis and Reactions of 5-Methylthieno[2',3':5,6]pyrimido[2,1-a]isoindol-4(5H)-one." Collection of Czechoslovak Chemical Communications 73, no. 2 (2008): 247–57. http://dx.doi.org/10.1135/cccc20080247.

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The reaction of 2-(bromomethyl)benzonitrile with methyl 3-aminothiophene-2-carboxylate results in two tautomeric thienopyrimidoisoindolones. Their methylation yields 5-methylthieno[2',3':5,6]pyrimido[2,1-a]isoindol-4(5H)-one which reacts with N-substituted maleimides and dimethyl acetylenedicarboxylate.

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34

Šinkovec, Rok, Uroš Grošelj, Benjamin Prek, et al. "A simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates: potential intermediates in the synthesis of polysubstituted five- and six-membered heterocycles." Zeitschrift für Naturforschung B 71, no. 6 (2016): 677–82. http://dx.doi.org/10.1515/znb-2016-0017.

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AbstractIn this communication, a simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates is described. Methyl ketones were transformed by treatment with N,N-dimethylacetamide dimethyl acetal (DMADMA) into 3-dimethylamino-1-(substituted)but-2-en-1-ones, followed by treatment with ammonium acetate into (Z)-3-amino-1-(substituted)but-2-en-1-ones and addition to dimethyl acetylenedicarboxylate. These novel polysubstituted butadienes are potential intermediates for the metal-free preparation of polysubstituted five- and six-membered heterocycles.

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35

Yates, Peter, Anabela Gomes, D. Jean Burnell, Dong Dao Cong, and Jeffery F. Sawyer. "Some 6,6-disubstituted 2,4-cyclohexadien-1-ones and the facial selectivity in their Diels–Alder reactions with dimethyl acetylenedicarboxylate." Canadian Journal of Chemistry 67, no. 1 (1989): 37–47. http://dx.doi.org/10.1139/v89-007.

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6,6-Disubstituted 2,4-cyclohexadien-1-ones can be prepared by dibromination–bisdehydrobromination of the corresponding 6,6-disubstituted 2,2-dibromocyclohexanones. Such dienes undergo Diels–Alder reactions with dimethyl acetylenedicarboxylate to give 3,3-disubstituted 5,6-di(methoxycarbonyl)bicyclo[2.2.2]octa-5,7-dien-2-ones; when the substituents at C-6 in the dienones are different, two diastereomers of the adducts are formed in a ratio dependent on the "facial selectivity" in the Diels–Alder reactions. For the cases where one of the 6-substituents is methyl and the other is methoxycarbonyl,

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36

Matusiak, Grazyna. "1,3-Dipolar Cycloaddition Reactions of the Ylide Derived from 6-Phenacyl-benzo[f][1,7]naphthyridinium Bromide." Australian Journal of Chemistry 52, no. 2 (1999): 149. http://dx.doi.org/10.1071/c98109.

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The 1,3-dipolar cycloaddition reactions of 4,6-diazaphenanthrene 6-phenacylide formed in situ from the quaternary 6-phenacylbenzo[f][1,7]naphthyridinium bromide in basic medium were examined; methacrylic acid, methyl methacrylate, butyl vinyl ether, methyl vinyl ketone, maleic anhydride and dimethyl acetylenedicarboxylate were used as the dipolarophiles.

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37

Musgrave, RP, NW Jacobsen, G. Bourne, CHL Kennard, G. Smith, and TCW Mak. "Cycloaddition Reactions of 3-Dimethylamino-1-methyl-1,2,4-triazinium-5-olates With Dimethyl Acetylenedicarboxylate." Australian Journal of Chemistry 48, no. 6 (1995): 1175. http://dx.doi.org/10.1071/ch9951175.

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The cycloaddition reactions of some 3-dimethylamino-1-methyl-1,2,4-triazinium-5-olates (1) with dimethyl acetylenedicarboxylate ( dmad ) were studied. The products in all cases were found tobe dimethyl 4-dimethylamino-1-methyl-6-oxo-1,3a,6,6a-tetrahydropyrrolo[3,4-c]pyrazole-3,3a-dicarboxylate derivatives (2). The structure determinations were carried out by 1H and 13C n.m.r. and mass spectrometry, and for one derivative by single-crystal X-ray diffractometry. The mechanism of the reaction is also discussed.

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38

Kraus, Tomáš, Miloš Buděšínský, and Jiří Závada. "Novel Amphiphilic Cyclodextrins: Per[6-deoxy-6-(4,5-dicarboxy-1,2,3-triazol-1-yl)-2,3-di-O-methyl] Derivatives." Collection of Czechoslovak Chemical Communications 63, no. 4 (1998): 534–40. http://dx.doi.org/10.1135/cccc19980534.

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Per[6-deoxy-6-(4,5-dicarboxy-1,2,3-triazol-1-yl)-2,3-di-O-methyl] substituted α- and β-cyclodextrins 6a and 6b were prepared by 1,3-dipolar cycloaddition reaction of the corresponding per(6-azido-6-deoxy-2,3-di-O-methyl)cyclodextrins 4a and 4b with dimethyl acetylenedicarboxylate.

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39

Vale, Luís S. H. P., Joana F. B. Barata, Carla I. M. Santos, et al. "Corroles in 1,3-dipolar cycloaddition reactions." Journal of Porphyrins and Phthalocyanines 13, no. 03 (2009): 358–68. http://dx.doi.org/10.1142/s1088424609000371.

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The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C60 in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole-3-carbaldehyde is also presented.

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40

Potáček, Milan, Tomáš Topinka, Jiří Dostál, and Jaromír Marek. "Phenanthridinium-Based Azomethine Ylides in 1,3-Dipolar Cycloaddition with Dimethyl Acetylenedicarboxylate." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2641–49. http://dx.doi.org/10.1135/cccc19942641.

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Azomethine ylides generated from 5-(alkoxycarbonylmethyl) phenanthridinium cations I were used in the 1,3-dipolar cycloadditions with dimethyl acetylenedicarboxylate as dipolarophile. The cycloadducts II were found to be very unstable species and readily oxidized to fully aromatic pyrrolo[1,2-f]phenanthridines III. Their structure was compared with the compounds formed by the oxidation of cycloadducts IV of the same ylide with dimethyl fumarate and maleate. In both cases pyrrolines V were found as intermediates. The structure of the products was determined by NMR and MS as well as by X-ray ana

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41

Wu, Quanping, Hui-Fang Liu, Yue Zhang, Shiyu Shen, and Song Xue. "Iodine Mediated Addition of Trialkylamines to Dimethyl Acetylenedicarboxylate." Letters in Organic Chemistry 10, no. 9 (2013): 617–21. http://dx.doi.org/10.2174/15701786113109990027.

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42

Hassan, Alaa, Nasr Mohamed, Maysa Makhlouf, Stefan Bräse, and Martin Nieger. "Reactions of Dimethyl Acetylenedicarboxylate with 2,5-Dithiobiurea Derivatives." Synthesis 46, no. 22 (2014): 3097–102. http://dx.doi.org/10.1055/s-0034-1378551.

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43

Stephanidou-Stephanatou, Julia, Constantinos Neochoritis, and Tryfon Zarganes-Tzitzikas. "Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis." Synthesis 46, no. 05 (2014): 537–85. http://dx.doi.org/10.1055/s-0033-1340615.

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44

Okuma, Kentaro, Kazuki Kojima, Isao Kaneko, and Hiroshi Ohta. "Reactions of selenobenzophenones with dimethyl acetylenedicarboxylate or norbornadiene." Tetrahedron Letters 33, no. 10 (1992): 1333–36. http://dx.doi.org/10.1016/s0040-4039(00)91615-0.

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45

Zinin, A. I., and E. V. Babaev. "Unexpected reaction of 6-nitroindolizine with dimethyl acetylenedicarboxylate." Russian Chemical Bulletin 46, no. 3 (1997): 609–10. http://dx.doi.org/10.1007/bf02495432.

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46

Itoh, Tsuneo, Ikuko Fujii, Yasuo Tomii, Haruo Ogura, Yoshihisa Mizuno, and Norio Kawahara. "Further study on 1,3-dialkylaminouracil with dimethyl acetylenedicarboxylate." Journal of Heterocyclic Chemistry 24, no. 4 (1987): 1215–17. http://dx.doi.org/10.1002/jhet.5570240454.

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47

Machara, Aleš, Michaela Pojarová, and Jiří Svoboda. "Synthesis and Cycloaddition Reaction of 3-Vinylthieno[3,2-b][1]benzothiophene." Collection of Czechoslovak Chemical Communications 72, no. 7 (2007): 952–64. http://dx.doi.org/10.1135/cccc20070952.

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A new method of synthesis of 3-substituted thieno[3,2-b][1]benzothiophenes based on a halogen dance process was developed. The cycloaddition reaction of the title compound with dimethyl acetylenedicarboxylate leads to the formation of a complex mixture of products resulting from a series of consecutive reactions of the primary adduct.

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48

Menzek, A., and M. Balci. "Cycloheptatriene Norcaradiene Equilibrium in Dimethyl trans-3,8-Dihydroheptalene-3,8-dicarboxylate." Australian Journal of Chemistry 46, no. 10 (1993): 1613. http://dx.doi.org/10.1071/ch9931613.

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Diels-Alder cycloadditions of dienophiles , such as 4-phenyl-1,2,4-triazoline-3,5-dione, dimethyl acetylenedicarboxylate, dimethyl fumarate , diethyl azodicarboxylate , maleic anhydride, benzyne and p-benzoquinone, to dimethyl trans-3,8-dihydrohexalene-3,8-dicarboxylate (4) have been investigated, and monoaddition products (9)-(16) have been isolated. It has been shown that a second addition to this system occurs only with singlet oxygen and with benzyne. Furthermore, it has been established that the second addition is retarded because of the strain in the cycloheptatriene molecule. The anti b

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49

Tomaščiková, Jana, Ján Imrich, Ivan Danihel, Stanislav Böhm, and Pavol Kristian. "Heterocyclization of (Acridin-9-yl)thiosemicarbazides with Dimethyl Acetylenedicarboxylate." Collection of Czechoslovak Chemical Communications 72, no. 3 (2007): 347–62. http://dx.doi.org/10.1135/cccc20070347.

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Two types of (acridin-9-yl)thiosemicarbazides with the acridine moiety in the thiourea part (Acr-NHCS, 10a, 10b) and hydrazine part (Acr-NHNHCS, 12a-12c) were prepared to investigate their reactions with dimethyl acetylenedicarboxylate. Five-membered thiazolidinone derivatives 15a, 15b, 19a-19c were formed; some aspects of corresponding reaction mechanisms are discussed. 1D and 2D 1H and 13C NMR spectroscopy and DFT quantum chemical calculations were used to elucidate the structure of the compounds.

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Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, Aissa Chibani, and Abdelmalek Bouraiou. "Synthesis and crystal structures of three novel benzimidazole/benzoindolizine hybrids." Zeitschrift für Naturforschung B 71, no. 3 (2016): 231–39. http://dx.doi.org/10.1515/znb-2015-0164.

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AbstractThree benzoindolizine derivatives, 1, 2, and 3, were obtained via 1,3-dipolar cycloaddition. The reaction of 1-(2′-benzimidazolylmethyl)isoquinolinium ylides with dimethyl acetylenedicarboxylate gave a mixture of pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (1) and 1,10b-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (2) derivatives containing a benzimidazole moiety. The reaction of this isoquinolinium N-ylide with dimethyl maleate gave an unexpected 2,3-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (3). The structures of all reported compounds have been examined by X-ray cr

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