, volume 19 , issue 2 , pages 312-315

Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

Hun Young Kim ¹

Eunsun Song ¹

Kyungsoo Oh ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Center for Metareceptome Research, College of Pharmacy, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea |

Publication type: Journal Article

Publication date: 2016-12-30

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.6b03348

Copy DOI

PubMed ID: 28035830

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

Found

1 citation

Sukhorukov Alexey

DSc in Chemistry

123 publications, 1 630 citations, 97 reviews

h-index: 22

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 731 citations

h-index: 30

Ural Federal University

Top-30

Journals

	2 4 6 8 10
Organic Letters	Organic Letters, 10, 17.24% Organic Letters 10 publications, 17.24%
Journal of Organic Chemistry	Journal of Organic Chemistry, 5, 8.62% Journal of Organic Chemistry 5 publications, 8.62%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 4, 6.9% Organic Chemistry Frontiers 4 publications, 6.9%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 3, 5.17% Asian Journal of Organic Chemistry 3 publications, 5.17%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 5.17% Organic and Biomolecular Chemistry 3 publications, 5.17%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 3.45% Advanced Synthesis and Catalysis 2 publications, 3.45%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 2, 3.45% European Journal of Organic Chemistry 2 publications, 3.45%
ChemistrySelect	ChemistrySelect, 2, 3.45% ChemistrySelect 2 publications, 3.45%
ACS Omega	ACS Omega, 2, 3.45% ACS Omega 2 publications, 3.45%
Beilstein Journal of Organic Chemistry	Beilstein Journal of Organic Chemistry, 1, 1.72% Beilstein Journal of Organic Chemistry 1 publication, 1.72%
Current Organic Chemistry	Current Organic Chemistry, 1, 1.72% Current Organic Chemistry 1 publication, 1.72%
Frontiers in Chemistry	Frontiers in Chemistry, 1, 1.72% Frontiers in Chemistry 1 publication, 1.72%
Molecules	Molecules, 1, 1.72% Molecules 1 publication, 1.72%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 1.72% Chemistry of Heterocyclic Compounds 1 publication, 1.72%
Monatshefte fur Chemie	Monatshefte fur Chemie, 1, 1.72% Monatshefte fur Chemie 1 publication, 1.72%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 1.72% Russian Chemical Reviews 1 publication, 1.72%
Mendeleev Communications	Mendeleev Communications, 1, 1.72% Mendeleev Communications 1 publication, 1.72%
Chinese Chemical Letters	Chinese Chemical Letters, 1, 1.72% Chinese Chemical Letters 1 publication, 1.72%
Tetrahedron	Tetrahedron, 1, 1.72% Tetrahedron 1 publication, 1.72%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 1.72% Chemistry - A European Journal 1 publication, 1.72%
Bulletin of the Korean Chemical Society	Bulletin of the Korean Chemical Society, 1, 1.72% Bulletin of the Korean Chemical Society 1 publication, 1.72%
Green Chemistry	Green Chemistry, 1, 1.72% Green Chemistry 1 publication, 1.72%
New Journal of Chemistry	New Journal of Chemistry, 1, 1.72% New Journal of Chemistry 1 publication, 1.72%
Synthetic Communications	Synthetic Communications, 1, 1.72% Synthetic Communications 1 publication, 1.72%
Zeitschrift fur Kristallographie - New Crystal Structures	Zeitschrift fur Kristallographie - New Crystal Structures, 1, 1.72% Zeitschrift fur Kristallographie - New Crystal Structures 1 publication, 1.72%
Advances in Heterocyclic Chemistry	Advances in Heterocyclic Chemistry, 1, 1.72% Advances in Heterocyclic Chemistry 1 publication, 1.72%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 1.72% Progress in Heterocyclic Chemistry 1 publication, 1.72%
Synlett	Synlett, 1, 1.72% Synlett 1 publication, 1.72%
Medicinal Research Reviews	Medicinal Research Reviews, 1, 1.72% Medicinal Research Reviews 1 publication, 1.72%
	2 4 6 8 10

Publishers

	2 4 6 8 10 12 14 16 18
American Chemical Society (ACS)	American Chemical Society (ACS), 17, 29.31% American Chemical Society (ACS) 17 publications, 29.31%
Wiley	Wiley, 14, 24.14% Wiley 14 publications, 24.14%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 10, 17.24% Royal Society of Chemistry (RSC) 10 publications, 17.24%
Elsevier	Elsevier, 5, 8.62% Elsevier 5 publications, 8.62%
Springer Nature	Springer Nature, 2, 3.45% Springer Nature 2 publications, 3.45%
Taylor & Francis	Taylor & Francis, 2, 3.45% Taylor & Francis 2 publications, 3.45%
Beilstein-Institut	Beilstein-Institut, 1, 1.72% Beilstein-Institut 1 publication, 1.72%
Bentham Science Publishers Ltd.	Bentham Science Publishers Ltd., 1, 1.72% Bentham Science Publishers Ltd. 1 publication, 1.72%
Frontiers Media S.A.	Frontiers Media S.A., 1, 1.72% Frontiers Media S.A. 1 publication, 1.72%
MDPI	MDPI, 1, 1.72% MDPI 1 publication, 1.72%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.72% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.72%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 1, 1.72% OOO Zhurnal "Mendeleevskie Soobshcheniya" 1 publication, 1.72%
Walter de Gruyter	Walter de Gruyter, 1, 1.72% Walter de Gruyter 1 publication, 1.72%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 1.72% Georg Thieme Verlag KG 1 publication, 1.72%
	2 4 6 8 10 12 14 16 18

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Kim H. Y., Song E., Oh K. Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones // Organic Letters. 2016. Vol. 19. No. 2. pp. 312-315.

GOST all authors (up to 50) Copy

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.6b03348

UR - https://doi.org/10.1021/acs.orglett.6b03348

TI - Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

T2 - Organic Letters

AU - Kim, Hun Young

AU - Song, Eunsun

AU - Oh, Kyungsoo

PY - 2016

DA - 2016/12/30

PB - American Chemical Society (ACS)

SP - 312-315

IS - 2

VL - 19

PMID - 28035830

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2016_Kim,

author = {Hun Young Kim and Eunsun Song and Kyungsoo Oh},

title = {Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones},

journal = {Organic Letters},

year = {2016},

volume = {19},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.6b03348},

number = {2},

pages = {312--315},

doi = {10.1021/acs.orglett.6b03348}

}

MLA

Cite this

MLA Copy

Kim, Hun Young, et al. “Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones.” Organic Letters, vol. 19, no. 2, Dec. 2016, pp. 312-315. https://doi.org/10.1021/acs.orglett.6b03348.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)