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Review
. 2014 Sep 3;19(9):13788-802.
doi: 10.3390/molecules190913788.

Cycloaddition of 1,3-butadiynes: efficient synthesis of carbo- and heterocycles

Tauqir A Nizami  1 , Ruimao Hua  2
Affiliations
Review

Cycloaddition of 1,3-butadiynes: efficient synthesis of carbo- and heterocycles

Tauqir A Nizami et al. Molecules. .

Abstract

Cycloaddition reactions of alkynes are elegant, atom-efficient transformations for the synthesis of carbo- and heterocycles, mostly aromatic, involving the construction of challenging skeletons of complex molecules. Therefore significant efforts have recently been devoted to the development of novel methodologies, efficient strategies and different catalytic systems to broaden the scope of these reactions. We summarize in this review the recent advances in the cycloaddition reactions of 1,3-butadiynes to provide facile and reliable approaches to various functionalized carbo- and heterocycles.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of substituted benzene from enynes and 1,3-diynes.
Scheme 2
Scheme 2
Synthesis of cyclophanes.
Scheme 3
Scheme 3
Synthesis of 3-oxobutanoates.
Scheme 4
Scheme 4
Synthesis of alkynyl benzene derivatives.
Scheme 5
Scheme 5
Synthesis of biaryl diphosphines.
Scheme 6
Scheme 6
Synthesis of aminonaphthalene derivatives.
Scheme 7
Scheme 7
Synthesis of bromonaphthalene.
Scheme 8
Scheme 8
Synthesis of 2,5-disubstituted furans.
Scheme 9
Scheme 9
Synthesis of 2,5-diarylfurans.
Scheme 10
Scheme 10
Synthesis of 2,5-diaminofurans.
Scheme 11
Scheme 11
Synthesis of 2,5-disubstituted furan derivatives.
Scheme 12
Scheme 12
Synthesis of α-pyrone derivatives.
Scheme 13
Scheme 13
Synthesis of disubstituted isoxazoles.
Scheme 14
Scheme 14
Synthesis of 1,2,5-trisubsituted pyrroles.
Scheme 15
Scheme 15
Synthesis of pyrrole derivatives.
Scheme 16
Scheme 16
Synthesis of isoquinoline derivatives.
Scheme 17
Scheme 17
Synthesis of 3,5-disubstituted pyrazoles.
Scheme 18
Scheme 18
Synthesis of 4,4'-bi-1,2,3-triazole derivatives.
Scheme 19
Scheme 19
Synthesis of naphthotriazoles.
Scheme 20
Scheme 20
Synthesis of benzo[f]quinazoline derivatives.
Scheme 21
Scheme 21
Synthesis of functionalized pyrimidines.
Scheme 22
Scheme 22
Synthesis of 2,2':5',2''-terthiophene.
Scheme 23
Scheme 23
Synthesis of thiophene derivatives.
Scheme 24
Scheme 24
Synthesis of substituted selenophenes.
Scheme 25
Scheme 25
Synthesis of spiro-type 2,5-diarylsiloles.
Scheme 26
Scheme 26
Synthesis of rhodacyclopenta-2,4-diene complex.
Scheme 27
Scheme 27
Synthesis of germole derivatives.
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References

    1. Brand J.P., Waser J. Electrophilic alkynylation: The dark side of acetylene chemistry. Chem. Soc. Rev. 2012;41:4165–4179. doi: 10.1039/c2cs35034c. - DOI - PubMed
    1. Chinchilla R., Nájera C. Chemicals from alkynes with palladium catalysts. Chem. Rev. 2013;114:1783–1826. doi: 10.1021/cr400133p. - DOI - PubMed
    1. Habrant D., Rauhala V., Koskinen A.M. Conversion of carbonyl compounds to alkynes: General overview and recent developments. Chem. Soc. Rev. 2010;39:2007–2017. doi: 10.1039/b915418c. - DOI - PubMed
    1. Stiegman A.E., Graham E., Perry K.J., Khundkar L.R., Cheng L.T., Perry J.W. The electronic structure and second-order nonlinear optical properties of donor-acceptor acetylenes: A detailed investigation of structure-property relationships. J. Am. Chem. Soc. 1991;113:7658–7666. doi: 10.1021/ja00020a030. - DOI
    1. Diederich F., Rubin Y. Synthetic approaches toward molecular and polymeric carbon allotropes. Angew. Chem. Int. Ed. 1992;31:1101–1123. doi: 10.1002/anie.199211013. - DOI

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