Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles

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Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles. / Khaidarov, Adel R.; Rostovskii, Nikolai V.; Starova, Galina L.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Chemistry of Heterocyclic Compounds, Vol. 54, No. 10, 01.10.2018, p. 946-950.

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

BibTeX

@article{91bdc895913040e39e377af11f3fd7ca,

title = "Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles",

abstract = "The first derivatives of 3H-pyrrol-4-amines spiro-fused with fluorene or anthrone were synthesized in a Rh2(OAc)4-catalyzed reaction of 1-sulfonyl-1,2,3-triazoles with 2H-azirines. The reaction proceeds through 1,4-diazahexa-1,3,5-triene intermediates, which under the conditions employed cyclize to stable at room temperature 1,2-dihydropyrazines. At elevated temperatures, 1,2-dihydropyrazines are in ring-chain equilibrium with 1,4-diazahexa-1,3,5-trienes, which undergo irreversible 5-exo-trig cyclization, leading to spirocyclic derivatives of 3H-pyrrol-4-amine.",

keywords = "1,2,3-triazoles, 2Н-azirines, catalysis, diazo compounds, pyrazines, pyrroles, spiro compounds, CYCLOADDITION, ROUTE, 2H-azirines, RING-EXPANSION",

author = "Khaidarov, {Adel R.} and Rostovskii, {Nikolai V.} and Starova, {Galina L.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",

year = "2018",

month = oct,

day = "1",

doi = "10.1007/s10593-018-2378-8",

language = "English",

volume = "54",

pages = "946--950",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Nature",

number = "10",

}

RIS

TY - JOUR

T1 - Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles

AU - Khaidarov, Adel R.

AU - Rostovskii, Nikolai V.

AU - Starova, Galina L.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2018/10/1

Y1 - 2018/10/1

N2 - The first derivatives of 3H-pyrrol-4-amines spiro-fused with fluorene or anthrone were synthesized in a Rh2(OAc)4-catalyzed reaction of 1-sulfonyl-1,2,3-triazoles with 2H-azirines. The reaction proceeds through 1,4-diazahexa-1,3,5-triene intermediates, which under the conditions employed cyclize to stable at room temperature 1,2-dihydropyrazines. At elevated temperatures, 1,2-dihydropyrazines are in ring-chain equilibrium with 1,4-diazahexa-1,3,5-trienes, which undergo irreversible 5-exo-trig cyclization, leading to spirocyclic derivatives of 3H-pyrrol-4-amine.

AB - The first derivatives of 3H-pyrrol-4-amines spiro-fused with fluorene or anthrone were synthesized in a Rh2(OAc)4-catalyzed reaction of 1-sulfonyl-1,2,3-triazoles with 2H-azirines. The reaction proceeds through 1,4-diazahexa-1,3,5-triene intermediates, which under the conditions employed cyclize to stable at room temperature 1,2-dihydropyrazines. At elevated temperatures, 1,2-dihydropyrazines are in ring-chain equilibrium with 1,4-diazahexa-1,3,5-trienes, which undergo irreversible 5-exo-trig cyclization, leading to spirocyclic derivatives of 3H-pyrrol-4-amine.

KW - 1,2,3-triazoles

KW - 2Н-azirines

KW - catalysis

KW - diazo compounds

KW - pyrazines

KW - pyrroles

KW - spiro compounds

KW - CYCLOADDITION

KW - ROUTE

KW - 2H-azirines

KW - RING-EXPANSION

UR - http://www.scopus.com/inward/record.url?scp=85056806804&partnerID=8YFLogxK

U2 - 10.1007/s10593-018-2378-8

DO - 10.1007/s10593-018-2378-8

M3 - Article

AN - SCOPUS:85056806804

VL - 54

SP - 946

EP - 950

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 10

ER -

ID: 36385389