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Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core. / Danilkina, N.A.; Kulyashova, A.E.; Khlebnikov, A.F.; Bräse, S.; Balova, I.A.

In: Journal of Organic Chemistry, Vol. 79, No. 19, 2014, p. 9018-9045.

Research output: Contribution to journal › Article › peer-review

Harvard

Danilkina, NA, Kulyashova, AE, Khlebnikov, AF, Bräse, S & Balova, IA 2014, 'Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core', Journal of Organic Chemistry, vol. 79, no. 19, pp. 9018-9045. https://doi.org/0.1021/jo501396s, https://doi.org/10.1021/jo501396s

APA

Danilkina, N. A., Kulyashova, A. E., Khlebnikov, A. F., Bräse, S., & Balova, I. A. (2014). Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core. Journal of Organic Chemistry, 79(19), 9018-9045. https://doi.org/0.1021/jo501396s, https://doi.org/10.1021/jo501396s

Vancouver

Danilkina NA, Kulyashova AE, Khlebnikov AF, Bräse S, Balova IA. Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core. Journal of Organic Chemistry. 2014;79(19):9018-9045. https://doi.org/0.1021/jo501396s, https://doi.org/10.1021/jo501396s

Author

Danilkina, N.A. ; Kulyashova, A.E. ; Khlebnikov, A.F. ; Bräse, S. ; Balova, I.A. / Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 19. pp. 9018-9045.

BibTeX

@article{5ce6b55e014745bea1281c5570cf0787,
title = "Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core",
abstract = "An efficient strategy for the synthesis of asymmetricallysubstituted enediynes fused to benzothiophene, benzofuran,and indole was developed. The proposed approach is based on theelectrophilic cyclization of diacetylenes and Sonogashira coupling.Thus, iodocyclization of readily available ortho-functionalized (buta-1,3-diynyl)arenes was used as a direct way for the synthesis of2-ethynyl-3-iodoheteroindenes. These substrates and their modifiedderivatives were easily converted by Sonogashira coupling with acetylenesto a variety of asymmetrically substituted acyclic enediynesfused to heterocycles. The tolerance of the developed methodologyto a variety of functional groups is a great advantage in the synthesisof macrocyclic enediyne systems fused to a heterocyclic core. Synthesisof indole-fused 12-membered macrocyclic dienediyne was achievedusing ring-closing metathesis as a key step.",
author = "N.A. Danilkina and A.E. Kulyashova and A.F. Khlebnikov and S. Br{\"a}se and I.A. Balova",
year = "2014",
doi = "0.1021/jo501396s",
language = "English",
volume = "79",
pages = "9018--9045",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

RIS

TY - JOUR

T1 - Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core

AU - Danilkina, N.A.

AU - Kulyashova, A.E.

AU - Khlebnikov, A.F.

AU - Bräse, S.

AU - Balova, I.A.

PY - 2014

Y1 - 2014

N2 - An efficient strategy for the synthesis of asymmetricallysubstituted enediynes fused to benzothiophene, benzofuran,and indole was developed. The proposed approach is based on theelectrophilic cyclization of diacetylenes and Sonogashira coupling.Thus, iodocyclization of readily available ortho-functionalized (buta-1,3-diynyl)arenes was used as a direct way for the synthesis of2-ethynyl-3-iodoheteroindenes. These substrates and their modifiedderivatives were easily converted by Sonogashira coupling with acetylenesto a variety of asymmetrically substituted acyclic enediynesfused to heterocycles. The tolerance of the developed methodologyto a variety of functional groups is a great advantage in the synthesisof macrocyclic enediyne systems fused to a heterocyclic core. Synthesisof indole-fused 12-membered macrocyclic dienediyne was achievedusing ring-closing metathesis as a key step.

AB - An efficient strategy for the synthesis of asymmetricallysubstituted enediynes fused to benzothiophene, benzofuran,and indole was developed. The proposed approach is based on theelectrophilic cyclization of diacetylenes and Sonogashira coupling.Thus, iodocyclization of readily available ortho-functionalized (buta-1,3-diynyl)arenes was used as a direct way for the synthesis of2-ethynyl-3-iodoheteroindenes. These substrates and their modifiedderivatives were easily converted by Sonogashira coupling with acetylenesto a variety of asymmetrically substituted acyclic enediynesfused to heterocycles. The tolerance of the developed methodologyto a variety of functional groups is a great advantage in the synthesisof macrocyclic enediyne systems fused to a heterocyclic core. Synthesisof indole-fused 12-membered macrocyclic dienediyne was achievedusing ring-closing metathesis as a key step.

U2 - 0.1021/jo501396s

DO - 0.1021/jo501396s

M3 - Article

VL - 79

SP - 9018

EP - 9045

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

ID: 7011337