EventsThe 22nd International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-22-05767
This submission belongs to the session C. General Organic Synthesis of the event The 22nd International Electronic Conference on Synthetic Organic Chemistry
Published date
14 Nov, 2018
Citation
Ramon J Estevez, Mónica Treus, Cristian O Salas, Juan C. Estévez, Rearrangement of 3-(4,5-dimethoxy-2-vinylphenyl)-2-methyl-5-nitroisoquinolin-1(2H)-one to 2-(6,7-dimethoxy-1-oxoisoquinolin-2(1H)-yl)-N-methylbenzamide: a mechanistic proposal, in Proceedings of The 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-22-05767
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Rearrangement of 3-(4,5-dimethoxy-2-vinylphenyl)-2-methyl-5-nitroisoquinolin-1(2H)-one to 2-(6,7-dimethoxy-1-oxoisoquinolin-2(1H)-yl)-N-methylbenzamide: a mechanistic proposal

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Ramon J Estevez 1
Mónica Treus 2
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Cristian O Salas 3
Juan C. Estévez 4
1. Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain., Seychelles
2. Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
3. Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, 702843 Santiago de Chile, Chile.
4. Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Abstract

Nitro compounds are compounds of great versatility in organic synthesis due to their easy availability and transformation into a wide variety of functionalities.[1] As a part of our continued interest in nitro compounds, we few years ago reported the transformation of 3-(4,5-dimethoxy-2-vinylphenyl)-2-methyl-5-nitroisoquinolin-1(2H)-one (1) into 2-(6,7-dimethoxy-1-oxoisoquinolin-2(1H)-yl)-N-methylbenzamide (4), via 3-(4,5-dimethoxy-2-vinyl- phenyl)-2-methyl-5-nitroisoquinolin-1(2H)-one (2) and 3-(2-(2,2-dimethoxyethyl)-4,5-dimethoxy-phenyl)-2-methyl-5-nitroisoquinolin-1(2H)-one (3).[2]

A mechanistic proposal for the novel, striking rearrangement of compound 3 to compound 4 will be discussed.

Keywords
Nitro compounds
isoquinolines
rearrangement
Manuscript
ECSOC-22 Comunication - RE vf.pdf
Poster
ECSOC-22 Comunication - RE vf.pdf
ECSOC-22 Comunication - RE vf.pdf
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