Fischer indolisation of N-(?-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F14%3A43871923" target="_blank" >RIV/70883521:28110/14:43871923 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1039/c4ob01714e" target="_blank" >http://dx.doi.org/10.1039/c4ob01714e</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c4ob01714e" target="_blank" >10.1039/c4ob01714e</a>

Result language

angličtina

Original language name

Fischer indolisation of N-(?-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study

Original language description

N-(?-ketoacyl)anthranilic acids reacted with phenylhydrazinium chloride in boiling acetic acid to afford 2-(indol-2-carboxamido)benzoic acids in good to excellent yields and 2-indolyl-3,1-benzoxazin-4-ones as by-products. The formation of the latter products could easily be suppressed by a hydrolytic workup. Alternatively, by increasing the reaction temperature and/or time, 2-indolyl-3,1-benzoxazin-4-ones can be obtained exclusively. Optimisations of the reaction conditions as well as the scope and thecourse of the transformations were investigated. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H-1H gs-COSY, 1H-13C gs-HSQC, 1H-13C gs-HMBC) with 1H-15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2014

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Organic and Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

12

Issue of the periodical within the volume

47

Country of publishing house

GB - UNITED KINGDOM

Number of pages

15

Pages from-to

9650-9664

UT code for WoS article

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EID of the result in the Scopus database

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