Aldazines in the Castagnoli-Cushman Reaction

Standard

Aldazines in the Castagnoli-Cushman Reaction. / Mikheyev, Alexander ; Kantin, Grigory ; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 50, No. 10, 17.05.2018, p. 2076-2086.

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

BibTeX

@article{9afd36fb952b4a0ca74e293aa63dd36d,

title = "Aldazines in the Castagnoli-Cushman Reaction",

abstract = "Aldazines were employed in the Castagnoli-Cushman reaction of homophthalic anhydride for the first time. The reaction proved to be distinctly diastereoselective when conducted at room temperature in acetonitrile, yielding predominantly the kinetic cis -configured adduct as a racemate. Thermodynamically more stable trans -configuration could be attained either via heating the cis -configured product in DMSO or via the action of a base (imidazole) in the course of CDI-promoted esterification or amidation of the carboxylic acid function in the initial adducts. Further manipulation of the remaining N -acylhydrazone moiety in the latter led to N -alkyl- or fully unprotected N -aminolactams.",

keywords = "aldazines, Castagnoli-Cushman reaction, homophthalic anhydride, hydrazone cleavage, hydrazone reduction, Naminolactams, non-symmetrical, symmetrical",

author = "Alexander Mikheyev and Grigory Kantin and Mikhail Krasavin",

year = "2018",

month = may,

day = "17",

doi = "10.1055/s-0037-1609375",

language = "English",

volume = "50",

pages = "2076--2086",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

}

RIS

TY - JOUR

T1 - Aldazines in the Castagnoli-Cushman Reaction

AU - Mikheyev, Alexander

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2018/5/17

Y1 - 2018/5/17

N2 - Aldazines were employed in the Castagnoli-Cushman reaction of homophthalic anhydride for the first time. The reaction proved to be distinctly diastereoselective when conducted at room temperature in acetonitrile, yielding predominantly the kinetic cis -configured adduct as a racemate. Thermodynamically more stable trans -configuration could be attained either via heating the cis -configured product in DMSO or via the action of a base (imidazole) in the course of CDI-promoted esterification or amidation of the carboxylic acid function in the initial adducts. Further manipulation of the remaining N -acylhydrazone moiety in the latter led to N -alkyl- or fully unprotected N -aminolactams.

AB - Aldazines were employed in the Castagnoli-Cushman reaction of homophthalic anhydride for the first time. The reaction proved to be distinctly diastereoselective when conducted at room temperature in acetonitrile, yielding predominantly the kinetic cis -configured adduct as a racemate. Thermodynamically more stable trans -configuration could be attained either via heating the cis -configured product in DMSO or via the action of a base (imidazole) in the course of CDI-promoted esterification or amidation of the carboxylic acid function in the initial adducts. Further manipulation of the remaining N -acylhydrazone moiety in the latter led to N -alkyl- or fully unprotected N -aminolactams.

KW - aldazines

KW - Castagnoli-Cushman reaction

KW - homophthalic anhydride

KW - hydrazone cleavage

KW - hydrazone reduction

KW - Naminolactams

KW - non-symmetrical

KW - symmetrical

UR - http://www.scopus.com/inward/record.url?scp=85044362911&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1609375

DO - 10.1055/s-0037-1609375

M3 - Article

AN - SCOPUS:85044362911

VL - 50

SP - 2076

EP - 2086

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 10

ER -

ID: 34633436