Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts

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Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts. / Filippov, Ilya P.; Agafonova, Anastasiya V.; Titov, Gleb D.; Smetanin, Ilia A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Journal of Organic Chemistry, Vol. 87, No. 9, 27.04.2022, p. 6514-6519.

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

BibTeX

@article{5615dc7b5d604b23a0f05fd93c0131b4,

title = "Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts",

abstract = "An efficient one-pot synthesis of imidazo[1,2-a]pyridines from 2-bromoazirines and pyridines has been developed. The construction of the bicyclic framework of imidazo[1,2-a]pyridines occurs in two steps through the formation of (2H-azirin-2-yl)pyridinium bromides followed by dehydrobrominative UV light-induced cyclization. The method can also be applied for the synthesis of imidazo[2,1-a]isoquinolines. Unstable in solution, (2H-azirin-2-yl)pyridinium/isoquinolinium bromides were quantitatively converted to stable tetrafluoroborates, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions. ",

author = "Filippov, {Ilya P.} and Agafonova, {Anastasiya V.} and Titov, {Gleb D.} and Smetanin, {Ilia A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = apr,

day = "27",

doi = "10.1021/acs.joc.2c00514",

language = "English",

volume = "87",

pages = "6514--6519",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

RIS

TY - JOUR

T1 - Synthesis of Imidazo[1,2- a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts

AU - Filippov, Ilya P.

AU - Agafonova, Anastasiya V.

AU - Titov, Gleb D.

AU - Smetanin, Ilia A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2022/4/27

Y1 - 2022/4/27

N2 - An efficient one-pot synthesis of imidazo[1,2-a]pyridines from 2-bromoazirines and pyridines has been developed. The construction of the bicyclic framework of imidazo[1,2-a]pyridines occurs in two steps through the formation of (2H-azirin-2-yl)pyridinium bromides followed by dehydrobrominative UV light-induced cyclization. The method can also be applied for the synthesis of imidazo[2,1-a]isoquinolines. Unstable in solution, (2H-azirin-2-yl)pyridinium/isoquinolinium bromides were quantitatively converted to stable tetrafluoroborates, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions.

AB - An efficient one-pot synthesis of imidazo[1,2-a]pyridines from 2-bromoazirines and pyridines has been developed. The construction of the bicyclic framework of imidazo[1,2-a]pyridines occurs in two steps through the formation of (2H-azirin-2-yl)pyridinium bromides followed by dehydrobrominative UV light-induced cyclization. The method can also be applied for the synthesis of imidazo[2,1-a]isoquinolines. Unstable in solution, (2H-azirin-2-yl)pyridinium/isoquinolinium bromides were quantitatively converted to stable tetrafluoroborates, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions.

UR - http://www.scopus.com/inward/record.url?scp=85129213008&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/3a1b413f-fe3e-3032-8333-67e9b3e63a59/

U2 - 10.1021/acs.joc.2c00514

DO - 10.1021/acs.joc.2c00514

M3 - Article

AN - SCOPUS:85129213008

VL - 87

SP - 6514

EP - 6519

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 9

ER -

ID: 95277536