𝔖 Bobbio Scriptorium
✦   LIBER   ✦

(±)-2-alkyl-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a catalyst and pressure dependent tandem reduction-reductive amination reaction

✍ Scribed by Richard A. Bunce; Takahiro Nago; Nathan Sonobe

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
471 KB
Volume
44
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

A series of 2‐(2‐nitrobenzyl)‐substituted β‐keto ester derivatives has been subjected to reductive cyclization under catalytic hydrogenation conditions. The reactions were found to be highly dependent on the catalyst and hydrogen pressure used. Hydrogenation over 5% palladium‐on‐carbon at 4 atmospheres pressure produced complex mixtures of products that included predominantly 1,2,3,4‐tetrahydroquinoline and quinoline products; at 1 atmosphere pressure, the same reactions gave mixtures containing predominantly tetrahydroquinoline and 1,4‐dihydroquinoline derivatives. Hydrogenation using 5% platinum‐on‐carbon was much cleaner and afforded the desired cis‐ and trans‐(±)‐2‐alkyl‐1,2,3,4‐tetrahydroquinoline‐3‐carboxylic esters, with the cis product predominating by ≥ 13:1.

📜 SIMILAR VOLUMES

(±)-2,3-dialkyl-1,2,3,4-tetrahydroquinol
(±)-2,3-dialkyl-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a tandem reduction-reductive amination reaction
✍ Richard A. Bunce; James E. Schammerhorn; LeGrande M. Slaughter 📂 Article 📅 2007 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 521 KB

## Abstract magnified image A series of 2‐methyl‐2‐(2‐nitrobenzyl)‐substituted β‐keto ester derivatives has been subjected to reductive cyclization under hydrogenation conditions to assess the importance of the ester group position on the diastereoselectivity of the process. Hydrogenation over 5%

6-Nitro-1,2,3,4-tetrahydroquinolines by
6-Nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-SNAr reaction
✍ Richard A. Bunce; Takahiro Nago 📂 Article 📅 2008 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 433 KB 👁 1 views

## Abstract magnified image A tandem reductive amination‐S~N~Ar reaction has been developed for the synthesis of 6‐nitro‐1,2,3,4‐tetrahydroquinolines. Treatment of 4‐(2‐fluoro‐5‐nitrophenyl)‐2‐butanone or 3‐(2‐fluoro‐5‐nitrophenyl)‐propanal with primary amines and sodium cyanoborohydride in methan

ChemInform Abstract: 6-Nitro-1,2,3,4-tet
ChemInform Abstract: 6-Nitro-1,2,3,4-tetrahydroquinoline-4-carboxylic Esters and 7-Nitro-3,4-dihydroquinoxaline-1(2H)-carboxylic Esters by a Tandem Reductive Amination—SNAr Reaction.
✍ Richard A. Bunce; James E. Schammerhorn 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 44 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v