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

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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.

Original languageEnglish
Pages (from-to)946-950
JournalChemistry of Heterocyclic Compounds
Volume54
Issue number10
DOIs
Publication statusPublished - 1 Oct 2018

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Azirines
Amines
Derivatives
Cyclization
Temperature
1-sulfonyl-1,2,3-triazole

Scopus subject areas

  • Organic Chemistry

Cite this

@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",
author = "Khaidarov, {Adel R.} and Rostovskii, {Nikolai V.} and Starova, {Galina L.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",
year = "2018",
month = "10",
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",
number = "10",

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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

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 -