Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations

Standard

Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations. / Bodunov, Vladimir A.; Galenko, Ekaterina E.; Sakharov, Pavel A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.

In: The Journal of organic chemistry, Vol. 84, No. 16, 16.08.2019, p. 10388-10401.

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

BibTeX

@article{e53179af8840492d8b85084ba528f143,

title = "Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations",

abstract = "The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2H-azirines, prepared by a simplified procedure from 2H-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)2, provided selectively previously unknown benzo[e]- and hetero[e]-fused indol-7-oles in good yields. Formylation of benzo[e]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[e]indol-4-oles gave various 4-substituted benzo[e]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[e]indoles, upon treatment with BF3·Et2O/Et3N, afforded a new type of fluorescent boron complexes with large Stokes shifts.",

keywords = "CHEMISTRY, DIAZO, H INSERTION, INDOLE, ORGANIC-SYNTHESIS",

author = "Bodunov, {Vladimir A.} and Galenko, {Ekaterina E.} and Sakharov, {Pavel A.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = aug,

day = "16",

doi = "10.1021/acs.joc.9b01573",

language = "English",

volume = "84",

pages = "10388--10401",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "16",

}

RIS

TY - JOUR

T1 - Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations

AU - Bodunov, Vladimir A.

AU - Galenko, Ekaterina E.

AU - Sakharov, Pavel A.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

PY - 2019/8/16

Y1 - 2019/8/16

N2 - The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2H-azirines, prepared by a simplified procedure from 2H-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)2, provided selectively previously unknown benzo[e]- and hetero[e]-fused indol-7-oles in good yields. Formylation of benzo[e]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[e]indol-4-oles gave various 4-substituted benzo[e]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[e]indoles, upon treatment with BF3·Et2O/Et3N, afforded a new type of fluorescent boron complexes with large Stokes shifts.

AB - The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2H-azirines, prepared by a simplified procedure from 2H-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)2, provided selectively previously unknown benzo[e]- and hetero[e]-fused indol-7-oles in good yields. Formylation of benzo[e]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[e]indol-4-oles gave various 4-substituted benzo[e]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[e]indoles, upon treatment with BF3·Et2O/Et3N, afforded a new type of fluorescent boron complexes with large Stokes shifts.

KW - CHEMISTRY

KW - DIAZO

KW - H INSERTION

KW - INDOLE

KW - ORGANIC-SYNTHESIS

UR - http://www.mendeley.com/research/selective-cucatalyzed-intramolecular-annulation-3arylheteryl2diazoacetyl1-h-pyrroles-synthesis-benzo

UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b01573

UR - http://www.scopus.com/inward/record.url?scp=85070545821&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b01573

DO - 10.1021/acs.joc.9b01573

M3 - Article

VL - 84

SP - 10388

EP - 10401

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 16

ER -

ID: 45063876