Mechanochemical Synthesis of Primary Amides

Jorge Gómez-Carpintero; J. Domingo Sánchez; J. Francisco González; J. Carlos Menéndez

doi:10.1021/acs.joc.1c02350

Mechanochemical Synthesis of Primary Amides

Jorge Gómez-Carpintero
, J. Domingo Sánchez
, J. Francisco González
, J. Carlos Menéndez

Geriatric and General Medicine

Complutense University

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

45 Scopus citations

Abstract

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

Original language	English
Pages (from-to)	14232-14237
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	86
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.1c02350
State	Published - Oct 15 2021

Access to Document

10.1021/acs.joc.1c02350

Cite this

@article{97521d5a935247489ebd1c04b9c528cb,

title = "Mechanochemical Synthesis of Primary Amides",

abstract = "Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.",

author = "Jorge G{\'o}mez-Carpintero and S{\'a}nchez, \{J. Domingo\} and Gonz{\'a}lez, \{J. Francisco\} and Men{\'e}ndez, \{J. Carlos\}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = oct,

day = "15",

doi = "10.1021/acs.joc.1c02350",

language = "English",

volume = "86",

pages = "14232--14237",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "20",

}

TY - JOUR

T1 - Mechanochemical Synthesis of Primary Amides

AU - Gómez-Carpintero, Jorge

AU - Sánchez, J. Domingo

AU - González, J. Francisco

AU - Menéndez, J. Carlos

PY - 2021/10/15

Y1 - 2021/10/15

N2 - Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

AB - Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

UR - https://www.scopus.com/pages/publications/85117078662

U2 - 10.1021/acs.joc.1c02350

DO - 10.1021/acs.joc.1c02350

M3 - Article

AN - SCOPUS:85117078662

SN - 0022-3263

VL - 86

SP - 14232

EP - 14237

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Mechanochemical Synthesis of Primary Amides

Abstract

Access to Document

Other files and links

Fingerprint

Cite this