𝔖 Bobbio Scriptorium
✦   LIBER   ✦

(±)-1,2-Dialkyl-5-nitro-2,3-dihydro-1H-indoles by a tandem reductive amination-SNAr reaction

✍ Scribed by Richard A. Bunce; Takahiro Nago; Brian White

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
119 KB
Volume
46
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

A tandem reductive amination‐S~N~Ar reaction has been applied to the synthesis of (±)‐1,2‐dialkyl‐5‐nitro‐2,3‐dihydro‐1__H__‐indoles. Treatment of a series of 2‐fluoro‐5‐nitrobenzyl ketones with primary amines and sodium cyanoborohydride in methanol at room temperature provided good yields of the target heterocycles. The reaction is sensitive to steric hindrance and proceeds best with less hindered ketone substrates using primary amines that are unbranched at the α carbon. J. Heterocyclic Chem., (2009).

📜 SIMILAR VOLUMES

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

## 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

1-Alkyl-2,3-dihydro-4(1H)-quinolinones b
1-Alkyl-2,3-dihydro-4(1H)-quinolinones by a tandem Michael-SNAr annulation reaction
✍ Richard A. Bunce; Takahiro Nago 📂 Article 📅 2009 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 110 KB 👁 1 views

## Abstract magnified image A tandem Michael‐S~N~Ar annulation reaction has been developed for the synthesis of 1‐alkyl‐2,3‐dihydro‐4(1__H__)‐quinolinones. Success in the reaction followed expected electronic effects for the final S~N~Ar ring closure. Treatment of doubly activated 1‐(2‐fluoro‐5‐ni

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