Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs)

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.

langue originaleAnglais
Pages (de - à)1870-1873
Nombre de pages4
journalOrganic Letters
Volume17
Numéro de publication8
Les DOIs
étatPublié - 17 avr. 2015

Empreinte digitale

Anhydrides
anhydrides
naphthalene
Condensation reactions
synthesis
Amines
esters
amines
Esters
condensation
acids
Acids
naphthalenediimide

Citer ceci

@article{267dd62a5f464756b2c7bea252856a0a,
title = "Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs)",
abstract = "Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.",
author = "Berezin, {Andrey A.} and Andrea Sciutto and Nicola Demitri and Davide Bonifazi",
year = "2015",
month = "4",
day = "17",
doi = "10.1021/acs.orglett.5b00543",
language = "English",
volume = "17",
pages = "1870--1873",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "8",

}

Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs). / Berezin, Andrey A.; Sciutto, Andrea; Demitri, Nicola; Bonifazi, Davide.

Dans: Organic Letters, Vol 17, Numéro 8, 17.04.2015, p. 1870-1873.

Résultats de recherche: Contribution à un journal/une revueArticle

TY - JOUR

T1 - Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs)

AU - Berezin, Andrey A.

AU - Sciutto, Andrea

AU - Demitri, Nicola

AU - Bonifazi, Davide

PY - 2015/4/17

Y1 - 2015/4/17

N2 - Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.

AB - Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.

UR - http://www.scopus.com/inward/record.url?scp=84928040782&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b00543

DO - 10.1021/acs.orglett.5b00543

M3 - Article

C2 - 25822286

AN - SCOPUS:84928040782

VL - 17

SP - 1870

EP - 1873

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -