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

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

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.

Original language	English
Pages (from-to)	5487–5500
Number of pages	14
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201402654
Publication status	Published - 2014

Keywords

Amides
Conformation analysis
Furans
Heterocycles
Pyrroles
Rearrangement
Thiophenes

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10.1002/ejoc.201402654

Cite this

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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",

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language = "English",

volume = "2014",

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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

Abstract

Keywords

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Physical Chemistry and characterization(PC2)

CCDC 950747: Experimental Crystal Structure Determination

CCDC 950748: Experimental Crystal Structure Determination

CCDC 950749: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Equipment

Physical Chemistry and characterization(PC2)

Datasets

CCDC 950747: Experimental Crystal Structure Determination

CCDC 950748: Experimental Crystal Structure Determination

CCDC 950749: Experimental Crystal Structure Determination

Cite this