2,5-Diamide-substituted five-membered heterocycles: Challenging molecular synthons

Chiara Fabbro; Simone Armani; Laure Elie Carloni; Federica De Leo; Johan Wouters; Davide Bonifazi

doi:10.1002/ejoc.201402654

2,5-Diamide-substituted five-membered heterocycles: Challenging molecular synthons

Chiara Fabbro, Simone Armani, Laure Elie Carloni, Federica De Leo, Johan Wouters, Davide Bonifazi

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

langue originale	Anglais
Pages (de - à)	5487–5500
Nombre de pages	14
journal	European Journal of Organic Chemistry
Volume	2014
Numéro de publication	25
Les DOIs	https://doi.org/10.1002/ejoc.201402654
Etat de la publication	Publié - 2014

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10.1002/ejoc.201402654

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Physico-chimie et caractérisation (PC2)
Johan Wouters (!!Manager) & Carmela Aprile (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique

CCDC 950751: Experimental Crystal Structure Determination
Armani, S. (Contributeur), BONIFAZI, D. (Contributeur), Carloni, L. (Contributeur), De Leo, F. (Contributeur), Fabbro, C. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2014
DOI: 10.5517/cc10xbdn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10xbdn&sid=DataCite
Ensemble de données
CCDC 950750: Experimental Crystal Structure Determination
Armani, S. (Contributeur), BONIFAZI, D. (Contributeur), Carloni, L. (Contributeur), De Leo, F. (Contributeur), Fabbro, C. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2014
DOI: 10.5517/cc10xbcm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10xbcm&sid=DataCite
Ensemble de données
CCDC 950747: Experimental Crystal Structure Determination
Armani, S. (Contributeur), BONIFAZI, D. (Contributeur), Carloni, L. (Contributeur), De Leo, F. (Contributeur), Fabbro, C. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2014
DOI: 10.5517/cc10xb8j, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10xb8j&sid=DataCite
Ensemble de données

Contient cette citation

@article{18b96ad844244ebcb42bdf0b9984db32,

title = "2,5-Diamide-substituted five-membered heterocycles: Challenging molecular synthons",

abstract = "We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a {"}closed{"} conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.",

keywords = "Amides, Conformation analysis, Furans, Heterocycles, Pyrroles, Rearrangement, Thiophenes",

author = "Chiara Fabbro and Simone Armani and Carloni, {Laure Elie} and {De Leo}, Federica and Johan Wouters and Davide Bonifazi",

year = "2014",

doi = "10.1002/ejoc.201402654",

language = "English",

volume = "2014",

pages = "5487–5500",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "25",

}

TY - JOUR

T1 - 2,5-Diamide-substituted five-membered heterocycles: Challenging molecular synthons

AU - Fabbro, Chiara

AU - Armani, Simone

AU - Carloni, Laure Elie

AU - De Leo, Federica

AU - Wouters, Johan

AU - Bonifazi, Davide

PY - 2014

Y1 - 2014

N2 - We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

AB - We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

KW - Amides

KW - Conformation analysis

KW - Furans

KW - Heterocycles

KW - Pyrroles

KW - Rearrangement

KW - Thiophenes

UR - http://www.scopus.com/inward/record.url?scp=84904530888&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201402654

DO - 10.1002/ejoc.201402654

M3 - Article

SN - 1434-193X

VL - 2014

SP - 5487

EP - 5500

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

2,5-Diamide-substituted five-membered heterocycles: Challenging molecular synthons

Résumé

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Autres fichiers et liens

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Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 950751: Experimental Crystal Structure Determination

CCDC 950750: Experimental Crystal Structure Determination

CCDC 950747: Experimental Crystal Structure Determination

Contient cette citation