𝔖 Bobbio Scriptorium
✦   LIBER   ✦

4H-1-Benzopyrans by a tandem SN2-SNAr reaction

✍ Scribed by Richard A. Bunce; David Rogers; Takahiro Nago; Scott A. Bryant

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
313 KB
Volume
45
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

Treatment of 2‐fluoro‐5‐nitrobenzyl bromide with active methylene compounds in the presence of excess potassium carbonate in acetone leads to the formation of highly functionalized 4__H__‐1‐benzopyrans by a tandem S~N~2‐S~N~Ar reaction sequence. The reaction works well with β‐keto esters, β‐keto sulfones, β‐keto phosphine oxides, β‐keto phosphonates and β‐keto nitriles. The reaction is simple to perform and affords products in 50‐92% yields.

📜 SIMILAR VOLUMES

Benzo-fused heterocycles and carbocycles
Benzo-fused heterocycles and carbocycles by intramolecular SNAr and tandem SN2-SNAr reactions
✍ Richard A. Bunce; Takahiro Nago; Nathan Sonobe; Legrande M. Slaughter 📂 Article 📅 2008 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 375 KB 👁 1 views

## Abstract magnified image Benzo‐fused heterocyclic and carbocyclic systems have been synthesized by intramolecular S~N~Ar and tandem S~N~2‐S~N~Ar reactions. Treatment of 3‐(2‐fluoro‐5‐nitrophenyl)‐1‐propanol with sodium hydride in __N,N__‐dimethylformamide gave 6‐nitrochroman in 80% yield by an

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

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