𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Two- and Three-Component Reactions Leading to New Enamines Derived from 2,3-Dicyanobut-2-enoates

✍ Scribed by Grzegorz Mlostoń; Małgorzata Celeda; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
308 KB
Volume
92
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The three‐component reactions of 1‐azabicyclo[1.1.0]butanes 1, dicyanofumarates (E)‐5, and MeOH or morpholine yielded azetidine enamines 8 and 9 with the cis‐orientation of the ester groups at the CC bond ((E)‐configuration; Schemes 3 and 4). The structures of 8a and 9d were confirmed by X‐ray crystallography. The formation of the products is explained via the nucleophilic addition of 1 onto (E)‐5, leading to a zwitterion of type 7 (Scheme 2), which is subsequently trapped by MeOH or morpholine (10a), followed by elimination of HCN. Similarly, two‐component reactions between secondary amines 10a–10c and (E)‐5 gave products 12 with an (E)‐enamine structure and (Z)‐oriented ester groups. On the other hand, two‐component reactions involving primary amines 10d–10f or NH~3~ led to the formation of the corresponding (Z)‐enamines, in which the (E)‐orientation of ester groups was established.

📜 SIMILAR VOLUMES

ChemInform Abstract: Reaction of Aldimin
ChemInform Abstract: Reaction of Aldimine Anions with Vinamidinium Chloride: Three-Component Access to 3-Alkylpyridines and 3-Alkylpyridinium Salts and Access to 2-Alkyl Glutaconaldehyde Derivatives.
✍ Jean-Charles Wypych; Tuan Minh Nguyen; Michel Benechie; Christian Marazano 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 43 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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

Transformations of 2-aryl-4-(2-oxopyrrol
Transformations of 2-aryl-4-(2-oxopyrrolidinyl-1)-1,2,3,4-tetrahydroquinolines, cycloadducts of the BiCl3-catalyzed three-component Povarov reaction: Oxidation and reduction processes towards new potentially bioactive 2-arylquinoline derivatives
✍ Vladimir V. Kouznetsov; Carlos M. Meléndez Gómez; John H. Bermúdez Jaimes 📂 Article 📅 2010 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 132 KB

## Abstract magnified image Synthesis and spectral characterization of new series of 2‐aryl‐4‐(2‐oxopyrrolidinyl‐1)‐1,2,3,4‐tetrahydroquinolines and their aromatic analogs, 2‐arylquinolines are reported. It was found that substituted tetrahydroquinoline precursors are easily prepared using BiCl~3~‐