Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

Langui Xie; Saad Shaaban; Xiangyu Chen; Nuno Maulide

doi:10.1002/anie.201606604

Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

Langui Xie, Saad Shaaban, Xiangyu Chen, Nuno Maulide (Corresponding author)

Department of Organic Chemistry

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Brønsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.

Original language	English
Pages (from-to)	12864-12867
Number of pages	4
Journal	Angewandte Chemie (International Edition)
Volume	55
Issue number	41
DOIs	https://doi.org/10.1002/anie.201606604
Publication status	Published - 4 Oct 2016

Austrian Fields of Science 2012

104015 Organic chemistry

Keywords

alkynes
cycloaddition
heteroalkynes
nitriles
pyridines
ONE-STEP SYNTHESIS
ONE-POT SYNTHESIS
DE-NOVO SYNTHESIS
FUNCTIONALIZED PYRIDINES
UNACTIVATED NITRILES
CYCLOTRIMERIZATION REACTIONS
REGIOSELECTIVE SYNTHESIS
CATALYZED CYCLOADDITION
TITANIUM(II) ALKOXIDE
INTERNAL THIOALKYNES

Access to Document

10.1002/anie.201606604

Cite this

@article{d2c29c3d3cf5491abe0063f562289aca,

title = "Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions",

abstract = "The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Br{\o}nsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.",

keywords = "alkynes, cycloaddition, heteroalkynes, nitriles, pyridines, ONE-STEP SYNTHESIS, ONE-POT SYNTHESIS, DE-NOVO SYNTHESIS, FUNCTIONALIZED PYRIDINES, UNACTIVATED NITRILES, CYCLOTRIMERIZATION REACTIONS, REGIOSELECTIVE SYNTHESIS, CATALYZED CYCLOADDITION, TITANIUM(II) ALKOXIDE, INTERNAL THIOALKYNES",

author = "Langui Xie and Saad Shaaban and Xiangyu Chen and Nuno Maulide",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = oct,

day = "4",

doi = "10.1002/anie.201606604",

language = "English",

volume = "55",

pages = "12864--12867",

journal = "Angewandte Chemie (International Edition)",

issn = "1433-7851",

publisher = "WILEY-V C H VERLAG GMBH",

number = "41",

}

TY - JOUR

T1 - Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

AU - Xie, Langui

AU - Shaaban, Saad

AU - Chen, Xiangyu

AU - Maulide, Nuno

PY - 2016/10/4

Y1 - 2016/10/4

N2 - The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Brønsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.

AB - The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Brønsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.

KW - alkynes

KW - cycloaddition

KW - heteroalkynes

KW - nitriles

KW - pyridines

KW - ONE-STEP SYNTHESIS

KW - ONE-POT SYNTHESIS

KW - DE-NOVO SYNTHESIS

KW - FUNCTIONALIZED PYRIDINES

KW - UNACTIVATED NITRILES

KW - CYCLOTRIMERIZATION REACTIONS

KW - REGIOSELECTIVE SYNTHESIS

KW - CATALYZED CYCLOADDITION

KW - TITANIUM(II) ALKOXIDE

KW - INTERNAL THIOALKYNES

UR - http://www.scopus.com/inward/record.url?scp=84988844051&partnerID=8YFLogxK

U2 - 10.1002/anie.201606604

DO - 10.1002/anie.201606604

M3 - Article

SN - 1433-7851

VL - 55

SP - 12864

EP - 12867

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 41

ER -

Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions

Abstract

Austrian Fields of Science 2012

Keywords

Access to Document

Other files and links

Cite this