Preparation of 2-Amino-1,3-butadienes as N-Pyridine Derivatives

2-Amino-1,3-butadienes as pyridine derivatives have been prepared from corresponding dihydrothiazolo[3,2-a]pyridinium salts in reactions with a strong base. The pyridinium salts were prepared from pyridine-2(1H)-thiones and trans-1,4-dibromo-2-butene by a vicinal and chemoselective formation of 3-vi...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2008-05, Vol.38 (11), p.1846-1854
Main Authors: Dugstad, Harald, Undheim, Kjell
Format: Article
Language:English
Subjects:
2-Amino-1,3-butadienes
3-vinyldihydrothiazolo[3,2-a]pyridinium salts
N-(1,3-butadien-2-yl)pyridine-2(1H)-thiones
N-(1,3-butadien-2-yl)pyridinium derivatives
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:2-Amino-1,3-butadienes as pyridine derivatives have been prepared from corresponding dihydrothiazolo[3,2-a]pyridinium salts in reactions with a strong base. The pyridinium salts were prepared from pyridine-2(1H)-thiones and trans-1,4-dibromo-2-butene by a vicinal and chemoselective formation of 3-vinyldihydrothiazolo[3,2-a]pyridinium salts. A strong base was used for selective proton removal from the vinyl-substituted 3-position. A subsequent ring opening provided 2-substituted 1,3-butadienes with the azine appended at the annular nitrogen. Simple S-alkylation yielded a corresponding azinium salt, thereby introducing electrophilic character to the 1,3-butadiene system. Hydrolysis of the sulfide function provided the corresponding pyridin-2(1H)-one attached to the 1,3-butadiene in the 2-position.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910801981672