Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2- aminobenz...

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Autores principales:	Kaufman, Teodoro Saúl, Larghi, Enrique Leandro, Bracca, Andrea Beatriz Juana, Heredia, Daniel Alejandro, Mendez, María Virginia
Formato:	article artículo publishedVersion
Lenguaje:	Inglés
Publicado:	The Royal Society of Chemistry 2017
Materias:	Total synthesis Natural product Heterocycles Neocryptolepine Quinindoline Indoloquinolines
Acceso en línea:	http://hdl.handle.net/2133/9279 http://hdl.handle.net/2133/9279
Aporte de:	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario

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record_format	dspace
institution	Universidad Nacional de Rosario
institution_str	I-15
repository_str	R-121
collection	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language	Inglés
orig_language_str_mv	eng
topic	Total synthesis Natural product Heterocycles Neocryptolepine Quinindoline Indoloquinolines
spellingShingle	Total synthesis Natural product Heterocycles Neocryptolepine Quinindoline Indoloquinolines Kaufman, Teodoro Saúl Larghi, Enrique Leandro Bracca, Andrea Beatriz Juana Heredia, Daniel Alejandro Mendez, María Virginia Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
topic_facet	Total synthesis Natural product Heterocycles Neocryptolepine Quinindoline Indoloquinolines
description	A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2- aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2- nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2- one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C–N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.
format	article artículo publishedVersion
author	Kaufman, Teodoro Saúl Larghi, Enrique Leandro Bracca, Andrea Beatriz Juana Heredia, Daniel Alejandro Mendez, María Virginia
author_facet	Kaufman, Teodoro Saúl Larghi, Enrique Leandro Bracca, Andrea Beatriz Juana Heredia, Daniel Alejandro Mendez, María Virginia
author_sort	Kaufman, Teodoro Saúl
title	Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_short	Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_full	Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_fullStr	Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_full_unstemmed	Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_sort	efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
publisher	The Royal Society of Chemistry
publishDate	2017
url	http://hdl.handle.net/2133/9279 http://hdl.handle.net/2133/9279
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Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

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