89059-09-6

Usage

Class

Organic compounds

Subclass

Pyrrolizines

Structure

Heterocyclic aromatic compound with a five-membered ring containing nitrogen and oxygen atoms

Occurrence

Found in tobacco and tobacco products

Pharmacological and toxicological effects

Has been studied for its potential effects

Synthesis

Used as a precursor in the synthesis of other compounds

Scientific interest

Its chemical structure and properties make it a topic of interest in various scientific disciplines

Upstream product

• 5145-67-5 1-ethoxycarbonylmethyl-1H-pyrrole 
• 19167-98-7 pyrrol-1-yl-acetic acid 
• 79673-53-3 pyrrole-2-acetic acid 
• 89059-05-2 1-diazo-3-(pyrrol-1-yl)-2-propanone 

Relevant academic research and scientific papers

Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.

Intramolecular carbenoid insertions: The reactions of α-diazoketones derived from pyrrolyl and indolyl carboxylic acids with rhodium(II) acetate

α-Diazoketones derived from pyrrolyl- and indolyl-carboxylic acids were prepared and their Rh2(OAc)4 catalyzed decomposition chemistry was studied. These reactions generally resulted in the alkylation of the heteroaromatic system by the ketocarbenoid and in some instances the systems underwent CH or NH insertions. Evidence that some of these reactions proceed via a cyclopropane intermediate is presented. The methodology described provides facile access to fused pyrrolyl- or indolyl-cycloalkanone systems wherein the carbonyl is beta to the heteroaromatic system. (C) 2000 Elsevier Science Ltd.

269. Intramolecular Carbenoid Reaction of Pyrrole Derivatives. Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone

The copper-catalyzed pyrolysis of 1-diazo-3-(pyrrol-1-yl)-2-propanone (1a) and 1-diazo-4-(pyrrol-1-yl)-2-butanone (1b) in benzene solution gave 1H-pyrrolizin-2-(3H)-one (4a) and 5,6-dihydroindolizin-7(8H)-one (4b), respectively, in quantative yield.Similar pyrolysis of 1-diazo-4-(3-methylindol-1-yl)-2-butanone (9) was less efficient giving 1-methylbenzo-5,6-dihydroindolizin-7(8H)-one (10) and 4-(3-methylindol-1-yl)-but-1-en-3-one (11) in 7percent and 24percent yield, respectively.