Synthesis, volume 46, issue 05, pages 537-585

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Constantinos Neochoritis ¹

Tryfon Zarganes Tzitzikas ¹

Tryfon Zarganes-Tzitzikas ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki |

Publication type: Journal Article

Publication date: 2014-02-07

Thieme

Journal: Synthesis

Quartile SCImago

Quartile WOS

Impact factor: 2.6

ISSN: 00397881, 1437210X

DOI: 10.1055/s-0033-1340615

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Catalysis

Organic Chemistry

Abstract

This review presents the recent progress in the chemistry of dimethyl acetylenedicarboxylate (DMAD). The interest in and applications of this powerful reagent with more than 135 years of history have greatly increased in the last 10 years, further proving its versatility. Undoubtedly, DMAD can be a multi-tool in the quest of molecular complexity and diversity. The extreme structural diversity of the products described in this review illustrates the powerful potential of DMAD as a building block in organic synthesis. 1 Introduction 2 Michael Reactions 2.1 Sulfur as Nucleophile 2.2 Nitrogen as Nucleophile 2.3 Oxygen as Nucleophile 2.4 Addition to Carbon–Carbon Double Bonds 3 Cycloaddition Reactions 3.1 Diels–Alder Reactions ([4+2] Cycloadditions) 3.2 1,3-Dipolar Reactions ([3+2] Cycloadditions) 3.3 [2+2] Cycloadditions 3.4 [8+2] Cycloadditions 4 DMAD and the Generation of Zwitterions; Multicomponent Reactions (MCRs) 4.1 Phosphines and Derivatives 4.2 Amines 4.3 Isocyanides 4.4 Carbenes 4.5 Miscellaneous Reactions 5 Conclusion

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Citations by journals

	1 2 3 4
Molecular Diversity	Molecular Diversity, 4, 8.16% Molecular Diversity 4 publications, 8.16%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 4, 8.16% European Journal of Organic Chemistry 4 publications, 8.16%
Molecules	Molecules, 3, 6.12% Molecules 3 publications, 6.12%
Journal of Heterocyclic Chemistry	Journal of Heterocyclic Chemistry, 3, 6.12% Journal of Heterocyclic Chemistry 3 publications, 6.12%
Organic Letters	Organic Letters, 3, 6.12% Organic Letters 3 publications, 6.12%
Mendeleev Communications	Mendeleev Communications, 2, 4.08% Mendeleev Communications 2 publications, 4.08%
Journal of Chemical Research	Journal of Chemical Research, 2, 4.08% Journal of Chemical Research 2 publications, 4.08%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 4.08% Chemistry - A European Journal 2 publications, 4.08%
ChemistrySelect	ChemistrySelect, 2, 4.08% ChemistrySelect 2 publications, 4.08%
Journal of Sulfur Chemistry	Journal of Sulfur Chemistry, 2, 4.08% Journal of Sulfur Chemistry 2 publications, 4.08%
Mini-Reviews in Organic Chemistry	Mini-Reviews in Organic Chemistry, 1, 2.04% Mini-Reviews in Organic Chemistry 1 publication, 2.04%
Journal of Molecular Graphics and Modelling	Journal of Molecular Graphics and Modelling, 1, 2.04% Journal of Molecular Graphics and Modelling 1 publication, 2.04%
Progress in Polymer Science	Progress in Polymer Science, 1, 2.04% Progress in Polymer Science 1 publication, 2.04%
Nature Synthesis	Nature Synthesis, 1, 2.04% Nature Synthesis 1 publication, 2.04%
Journal of Polymer Science, Part A: Polymer Chemistry	Journal of Polymer Science, Part A: Polymer Chemistry, 1, 2.04% Journal of Polymer Science, Part A: Polymer Chemistry 1 publication, 2.04%
European Journal of Inorganic Chemistry	European Journal of Inorganic Chemistry, 1, 2.04% European Journal of Inorganic Chemistry 1 publication, 2.04%
ChemInform	ChemInform, 1, 2.04% ChemInform 1 publication, 2.04%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 2.04% Journal of Organic Chemistry 1 publication, 2.04%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 2.04% Journal of the American Chemical Society 1 publication, 2.04%
Macromolecules	Macromolecules, 1, 2.04% Macromolecules 1 publication, 2.04%
Doklady Chemistry	Doklady Chemistry, 1, 2.04% Doklady Chemistry 1 publication, 2.04%
RSC Advances	RSC Advances, 1, 2.04% RSC Advances 1 publication, 2.04%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 1, 2.04% Organic Chemistry Frontiers 1 publication, 2.04%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 2.04% Organic and Biomolecular Chemistry 1 publication, 2.04%
International Journal of Molecular Sciences	International Journal of Molecular Sciences, 1, 2.04% International Journal of Molecular Sciences 1 publication, 2.04%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 2.04% Progress in Heterocyclic Chemistry 1 publication, 2.04%
Synthetic Communications	Synthetic Communications, 1, 2.04% Synthetic Communications 1 publication, 2.04%
Advances in Heterocyclic Chemistry	Advances in Heterocyclic Chemistry, 1, 2.04% Advances in Heterocyclic Chemistry 1 publication, 2.04%
Heterocycles	Heterocycles, 1, 2.04% Heterocycles 1 publication, 2.04%
Synlett	Synlett, 1, 2.04% Synlett 1 publication, 2.04%
	1 2 3 4

Citations by publishers

	2 4 6 8 10 12 14
Wiley	Wiley, 14, 28.57% Wiley 14 publications, 28.57%
Elsevier	Elsevier, 6, 12.24% Elsevier 6 publications, 12.24%
Springer Nature	Springer Nature, 6, 12.24% Springer Nature 6 publications, 12.24%
American Chemical Society (ACS)	American Chemical Society (ACS), 6, 12.24% American Chemical Society (ACS) 6 publications, 12.24%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 4, 8.16% Multidisciplinary Digital Publishing Institute (MDPI) 4 publications, 8.16%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 3, 6.12% Royal Society of Chemistry (RSC) 3 publications, 6.12%
Taylor & Francis	Taylor & Francis, 3, 6.12% Taylor & Francis 3 publications, 6.12%
SAGE	SAGE, 2, 4.08% SAGE 2 publications, 4.08%
Bentham Science	Bentham Science, 1, 2.04% Bentham Science 1 publication, 2.04%
Pleiades Publishing	Pleiades Publishing, 1, 2.04% Pleiades Publishing 1 publication, 2.04%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 1, 2.04% The Japan Institute of Heterocyclic Chemistry 1 publication, 2.04%
Thieme	Thieme, 1, 2.04% Thieme 1 publication, 2.04%
	2 4 6 8 10 12 14

We do not take into account publications without a DOI.
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Neochoritis C., Zarganes Tzitzikas T., Zarganes-Tzitzikas T. Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis // Synthesis. 2014. Vol. 46. No. 05. pp. 537-585.

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Neochoritis C., Zarganes Tzitzikas T., Zarganes-Tzitzikas T. Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis // Synthesis. 2014. Vol. 46. No. 05. pp. 537-585.

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TY - JOUR

DO - 10.1055/s-0033-1340615

UR - https://doi.org/10.1055/s-0033-1340615

TI - Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

T2 - Synthesis

AU - Neochoritis, Constantinos

AU - Zarganes Tzitzikas, Tryfon

AU - Zarganes-Tzitzikas, Tryfon

PY - 2014

DA - 2014/02/07 00:00:00

PB - Thieme

SP - 537-585

IS - 05

VL - 46

SN - 0039-7881

SN - 1437-210X

ER -

BibTex |

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BibTex Copy

@article{2014_Neochoritis,

author = {Constantinos Neochoritis and Tryfon Zarganes Tzitzikas and Tryfon Zarganes-Tzitzikas},

title = {Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis},

journal = {Synthesis},

year = {2014},

volume = {46},

publisher = {Thieme},

month = {feb},

url = {https://doi.org/10.1055/s-0033-1340615},

number = {05},

pages = {537--585},

doi = {10.1055/s-0033-1340615}

}

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Neochoritis, Constantinos, et al. “Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis.” Synthesis, vol. 46, no. 05, Feb. 2014, pp. 537-585. https://doi.org/10.1055/s-0033-1340615.

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Thieme

Journal

Synthesis

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Quartile WOS

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2.6

ISSN

00397881 (Print)
1437210X (Electronic)