Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Chetan C. Chintawar; Manoj V. Mane; Akash G. Tathe; Suprakash Biswas; Nitin T. Patil

doi:10.1021/acs.orglett.9b02677

Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Chetan C. Chintawar, Manoj V. Mane, Akash G. Tathe, Suprakash Biswas, Nitin T. Patil

Physical Sciences and Engineering

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

25 Scopus citations

Abstract

Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

Original language	English (US)
Pages (from-to)	7109-7113
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.9b02677
State	Published - Aug 27 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Generous financial support by the Council of Scientific and Industrial Research (CSIR), New Delhi [File No. 02(0336)/ 18/EMR-II] is gratefully acknowledged. We thank Dr. Apurba Lal Koner, IISER Bhopal, for helping us in the determination of photophysical properties of fluorophores. C.C.C. and S.B. thank UGC for the award of junior and senior research fellowships, respectively. A.G.T. thanks IISER Bhopal for a junior research fellowship.

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10.1021/acs.orglett.9b02677

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@article{0211aa295f8c4c62b64934c4fbdda5ef,

title = "Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines",

abstract = "Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.",

author = "Chintawar, {Chetan C.} and Mane, {Manoj V.} and Tathe, {Akash G.} and Suprakash Biswas and Patil, {Nitin T.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Generous financial support by the Council of Scientific and Industrial Research (CSIR), New Delhi [File No. 02(0336)/ 18/EMR-II] is gratefully acknowledged. We thank Dr. Apurba Lal Koner, IISER Bhopal, for helping us in the determination of photophysical properties of fluorophores. C.C.C. and S.B. thank UGC for the award of junior and senior research fellowships, respectively. A.G.T. thanks IISER Bhopal for a junior research fellowship.",

year = "2019",

month = aug,

day = "27",

doi = "10.1021/acs.orglett.9b02677",

language = "English (US)",

volume = "21",

pages = "7109--7113",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

AU - Chintawar, Chetan C.

AU - Mane, Manoj V.

AU - Tathe, Akash G.

AU - Biswas, Suprakash

AU - Patil, Nitin T.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Generous financial support by the Council of Scientific and Industrial Research (CSIR), New Delhi [File No. 02(0336)/ 18/EMR-II] is gratefully acknowledged. We thank Dr. Apurba Lal Koner, IISER Bhopal, for helping us in the determination of photophysical properties of fluorophores. C.C.C. and S.B. thank UGC for the award of junior and senior research fellowships, respectively. A.G.T. thanks IISER Bhopal for a junior research fellowship.

PY - 2019/8/27

Y1 - 2019/8/27

N2 - Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

AB - Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

UR - http://hdl.handle.net/10754/658626

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.9b02677

UR - http://www.scopus.com/inward/record.url?scp=85072515838&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b02677

DO - 10.1021/acs.orglett.9b02677

M3 - Article

C2 - 31453703

SN - 1523-7060

VL - 21

SP - 7109

EP - 7113

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Abstract

Bibliographical note

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CCDC 1882296: Experimental Crystal Structure Determination : (2-methoxyphenyl)(1-phenylindolizino[3,4,5-ab]isoindol-2-yl)methanone

CCDC 1905761: Experimental Crystal Structure Determination : (1-cyclopropylindolizino[3,4,5-ab]isoindol-2-yl)(phenyl)methanone

Cite this

Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Abstract

Bibliographical note

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Datasets

CCDC 1882296: Experimental Crystal Structure Determination : (2-methoxyphenyl)(1-phenylindolizino[3,4,5-ab]isoindol-2-yl)methanone

CCDC 1905761: Experimental Crystal Structure Determination : (1-cyclopropylindolizino[3,4,5-ab]isoindol-2-yl)(phenyl)methanone

Cite this