Preparation of pyrazine carboxamides: A reaction involving N-heterocyclic carbene (NHC) intermediates

Rajasekhar Reddy Naredla; Barada P. Dash; Douglas A. Klumpp

doi:10.1021/ol402200x

Preparation of pyrazine carboxamides: A reaction involving N-heterocyclic carbene (NHC) intermediates

Rajasekhar Reddy Naredla
, Barada P. Dash
, Douglas A. Klumpp

Chemistry (Twin Cities)

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

14 Scopus citations

Abstract

In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product.

Original language	English (US)
Pages (from-to)	4806-4809
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	18
DOIs	https://doi.org/10.1021/ol402200x
State	Published - Sep 20 2013

Publisher link

10.1021/ol402200x

Find It

Find It at U of M Libraries

Cite this

@article{70761042c7384b02aef68b940f5f7336,

title = "Preparation of pyrazine carboxamides: A reaction involving N-heterocyclic carbene (NHC) intermediates",

abstract = "In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product.",

author = "Naredla, \{Rajasekhar Reddy\} and Dash, \{Barada P.\} and Klumpp, \{Douglas A.\}",

year = "2013",

month = sep,

day = "20",

doi = "10.1021/ol402200x",

language = "English (US)",

volume = "15",

pages = "4806--4809",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Preparation of pyrazine carboxamides

T2 - A reaction involving N-heterocyclic carbene (NHC) intermediates

AU - Naredla, Rajasekhar Reddy

AU - Dash, Barada P.

AU - Klumpp, Douglas A.

PY - 2013/9/20

Y1 - 2013/9/20

N2 - In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product.

AB - In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product.

UR - https://www.scopus.com/pages/publications/84884583763

UR - https://www.scopus.com/pages/publications/84884583763#tab=citedBy

U2 - 10.1021/ol402200x

DO - 10.1021/ol402200x

M3 - Article

C2 - 24015823

AN - SCOPUS:84884583763

SN - 1523-7060

VL - 15

SP - 4806

EP - 4809

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Preparation of pyrazine carboxamides: A reaction involving N-heterocyclic carbene (NHC) intermediates

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this