Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls

Niels Marien; B. Narendraprasad Reddy; Freija De Vleeschouwer; Steven Goderis; Kristof Van Hecke; Guido Verniest

doi:10.1002/anie.201800340

Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls

Niels Marien
, B. Narendraprasad Reddy
, Freija De Vleeschouwer
, Steven Goderis
, Kristof Van Hecke
, Guido Verniest

Onderzoeksoutput: Article › peer review

42 Citaten (Scopus)

212 Downloads (Pure)

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An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

Originele taal-2	English
Pagina's (van-tot)	5660-5664
Aantal pagina's	5
Tijdschrift	Angewandte Chemie International Edition
Volume	57
Nummer van het tijdschrift	20
DOI's	https://doi.org/10.1002/anie.201800340
Status	Published - 14 mei 2018

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10.1002/anie.201800340

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SRP2: Tracers van verleden en heden global changes
Claeys, P. (Administrative Promotor), Elskens, M. (Co-Promoter), Huybrechts, P. (Co-Promoter), Gao, Y. (Co-Promoter), Kervyn De Meerendre, M. (Co-Promoter), Claeys, P. (Administrative Promotor), Baeyens, W. (Co-Promoter) & Dehairs, F. (Co-Promoter)
1/11/12 → 31/10/24
Project: Fundamenteel

AMGC - Inductively Coupled Plasma Mass Spectrometry Lab.
Claeys, P. (Scientific coordinator), Snoeck, C. (Scientific coordinator), Goderis, S. (Scientific coordinator), Kopec, M. (Infrastructure coordinator) & Borremans, W. (Infrastructure coordinator)
Archeologie, Milieuveranderingen, en Geo-Chemie
Uitrusting/faciliteit: e-resource/single sited

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title = "Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls",

abstract = "An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.",

keywords = "cycloaddition, domino reactions, nitrogen heterocycles, ynamides, ynamines",

author = "Niels Marien and Reddy, \{B. Narendraprasad\} and \{De Vleeschouwer\}, Freija and Steven Goderis and \{Van Hecke\}, Kristof and Guido Verniest",

year = "2018",

month = may,

day = "14",

doi = "10.1002/anie.201800340",

language = "English",

volume = "57",

pages = "5660--5664",

journal = "Angewandte Chemie International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "20",

}

TY - JOUR

T1 - Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls

AU - Marien, Niels

AU - Reddy, B. Narendraprasad

AU - De Vleeschouwer, Freija

AU - Goderis, Steven

AU - Van Hecke, Kristof

AU - Verniest, Guido

PY - 2018/5/14

Y1 - 2018/5/14

N2 - An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

AB - An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

KW - cycloaddition

KW - domino reactions

KW - nitrogen heterocycles

KW - ynamides

KW - ynamines

UR - https://www.scopus.com/pages/publications/85045432411

U2 - 10.1002/anie.201800340

DO - 10.1002/anie.201800340

M3 - Article

SN - 1433-7851

VL - 57

SP - 5660

EP - 5664

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 20

ER -

Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls

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