Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.

Antonio Palumbo Piccionello; Nicolo' Vivona; Silvestre Buscemi; Andrea Pace

Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.

Antonio Palumbo Piccionello, Nicolo' Vivona, Silvestre Buscemi, Andrea Pace

Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche

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22 Citazioni (Scopus)

Abstract

A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(r-aminobenzyl)-1,2,4-oxadiazole, which was condensedwith benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-typerearrangement to afford novel 4(5)-acylaminoimidazoles.

Lingua originale	English
pagine (da-a)	3491-
Numero di pagine	3
Rivista	Organic Letters
Volume	12
Stato di pubblicazione	Published - 2010

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All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Palumbo Piccionello, A., Vivona, N., Buscemi, S., & Pace, A. (2010). Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles. Organic Letters, 12, 3491-.

@article{20e09565b0104e2db1eff90589f8ce77,

title = "Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.",

abstract = "A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(r-aminobenzyl)-1,2,4-oxadiazole, which was condensedwith benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-typerearrangement to afford novel 4(5)-acylaminoimidazoles.",

keywords = "heterocyclic rearrangement, heterogeneous catalysis, imidazole, oxadiazole, transamination, heterocyclic rearrangement, heterogeneous catalysis, imidazole, oxadiazole, transamination",

author = "{Palumbo Piccionello}, Antonio and Nicolo' Vivona and Silvestre Buscemi and Andrea Pace",

year = "2010",

language = "English",

volume = "12",

pages = "3491--",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.

AU - Palumbo Piccionello, Antonio

AU - Vivona, Nicolo'

AU - Buscemi, Silvestre

AU - Pace, Andrea

PY - 2010

Y1 - 2010

N2 - A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(r-aminobenzyl)-1,2,4-oxadiazole, which was condensedwith benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-typerearrangement to afford novel 4(5)-acylaminoimidazoles.

AB - A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(r-aminobenzyl)-1,2,4-oxadiazole, which was condensedwith benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-typerearrangement to afford novel 4(5)-acylaminoimidazoles.

KW - heterocyclic rearrangement

KW - heterogeneous catalysis

KW - imidazole

KW - oxadiazole

KW - transamination

KW - heterocyclic rearrangement

KW - heterogeneous catalysis

KW - imidazole

KW - oxadiazole

KW - transamination

UR - http://hdl.handle.net/10447/52096

M3 - Article

VL - 12

SP - 3491-

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -

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