3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
We reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert&...
Main Authors: | , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2021-03-01
|
Series: | Molbank |
Subjects: | |
Online Access: | https://www.mdpi.com/1422-8599/2021/1/M1196 |
_version_ | 1797541944152293376 |
---|---|
author | Diana Becerra Hugo Rojas Juan-Carlos Castillo |
author_facet | Diana Becerra Hugo Rojas Juan-Carlos Castillo |
author_sort | Diana Becerra |
collection | DOAJ |
description | We reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert</i>-butyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>1</b> and <i>p</i>-methoxybenzaldehyde <b>2</b>. The one-pot reductive amination proceeded by the formation in situ of the <i>N</i>-(5-pyrazolyl)imine <b>4</b> as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized <i>N</i>-heterocyclic amine <b>3</b> was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis. |
first_indexed | 2024-03-10T13:22:46Z |
format | Article |
id | doaj.art-eead7fab062c4b3cab7f488fb1900efe |
institution | Directory Open Access Journal |
issn | 1422-8599 |
language | English |
last_indexed | 2024-03-10T13:22:46Z |
publishDate | 2021-03-01 |
publisher | MDPI AG |
record_format | Article |
series | Molbank |
spelling | doaj.art-eead7fab062c4b3cab7f488fb1900efe2023-11-21T09:56:26ZengMDPI AGMolbank1422-85992021-03-0120211M119610.3390/M11963-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amineDiana Becerra0Hugo Rojas1Juan-Carlos Castillo2Escuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaEscuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaEscuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaWe reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert</i>-butyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>1</b> and <i>p</i>-methoxybenzaldehyde <b>2</b>. The one-pot reductive amination proceeded by the formation in situ of the <i>N</i>-(5-pyrazolyl)imine <b>4</b> as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized <i>N</i>-heterocyclic amine <b>3</b> was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis.https://www.mdpi.com/1422-8599/2021/1/M11965-aminopyrazolesolvent-free condensationreductive amination<i>N</i>-(5-pyrazolyl)imine<i>N</i>-heterocyclic aminesecondary amine |
spellingShingle | Diana Becerra Hugo Rojas Juan-Carlos Castillo 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine Molbank 5-aminopyrazole solvent-free condensation reductive amination <i>N</i>-(5-pyrazolyl)imine <i>N</i>-heterocyclic amine secondary amine |
title | 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine |
title_full | 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine |
title_fullStr | 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine |
title_full_unstemmed | 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine |
title_short | 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine |
title_sort | 3 i tert i butyl i n i 4 methoxybenzyl 1 methyl 1 i h i pyrazol 5 amine |
topic | 5-aminopyrazole solvent-free condensation reductive amination <i>N</i>-(5-pyrazolyl)imine <i>N</i>-heterocyclic amine secondary amine |
url | https://www.mdpi.com/1422-8599/2021/1/M1196 |
work_keys_str_mv | AT dianabecerra 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine AT hugorojas 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine AT juancarloscastillo 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine |