90935-74-3

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 73, p. 675, 1995 DOI: 10.1139/v95-086

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 74-88-4 methyl iodide 
• 932-82-1 4,5-dibromo-1H-pyrrole-2-carbaldehyde 
• 178941-13-4 2-(2-Cyano-2-ethoxycarbonylvinyl)-3-methylpyrrole 
• 24014-18-4 3-methyl-pyrrole-2-carboxaldehyde 
• 1003-67-4 4-methylpyridine-1-oxide 
• 153850-69-2 2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole 
• 58488-39-4 2,5-bis(1,3-benzodithiol-2-yl)pyrrole 
• 178941-14-5 5-(2-Cyano-2-ethoxycarbonylvinyl)-4-methylpyrrole-2-carbaldehyde 
• 64804-02-0 4-methyl-6H-pyrrolo[1,2-c][1,2,3]triazole 
• 117720-09-9 5,10-Bis-dimethylamino-2,7-dimethyl-5H,10H-dipyrrolo[1,2-a;1',2'-d]pyrazine-3,8-dicarbaldehyde 
• 616-43-3 3-methylpyrrole 
• 51-17-2 benzoimidazole 

Downstream Products

• 90935-68-5 all-trans-11,14-imino-retinal 

Relevant academic research and scientific papers

Convenient route for the synthesis of 3-substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes

3-Substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes have been obtained by hydrolysis with HgO-35% aq. HBF4-DMSO of the intermediates 4 and 5 prepared by electrophilic substitution reactions on 2,5-bis(1,3-benzodithiol-2-yl)pyrrole.

A new convergent method for porphyrin synthesis based on a '3 + 1' condensation

A new methodology based on the '3 + 1' acid-catalytic condensation of tripyrranes and pyrrole-2,5-dicarbaldehyde has been used, for the first time, for the synthesis of two types of porphyrins: vic-dipropionic ester porphyrins 30 and 31 including an analo

Synthesis of 5-substituted pyrrole-2-carboxaldehydes. Part I. Generation of formal 5-lithiopyrrole-2-carboxaldehyde equivalents by bromine-lithium exchange of 2-bromo-6-(diisopropylamino)-1-azafulvene derivatives

The first known lithiated 1-azafulvene derivatives, e.g., 8 and 13a, were generated by a low-temperature bromine-lithium exchange procedure with tert-butyllithium.These lithio species show substantial stability at /=-90 deg C because, at these temperatures, the sterically demanding 6-diisopropylamino moiety, unlike the dimethylamino group, completely inhibits nucleophilic addition to C-6.At higher temperatures, the addition of tert-butyllithium to C-6 is significant and it can become the dominant process.The lithio species 8 is a useful formal equivalent of 5-lithiopyrrole-2-carboxaldehyde since, on reaction with electrophilic reagents and subsequent hydrolysis, a wide variety of regiochemically pure 5-substituted pyrrole-2-carboxaldehydes is formed.The 6-dialkylamino-1-azafulvenes described herein exist predominantly or exclusively as the syn conformer in solution at room temperature.This conformational preference is confirmed by a significance NOE effect between H-4 and H-6 in the parent diisopropylamino compound 3f.The origin of the syn conformational preference stems from a substantial contribution of the charge-separated form 16 to the ground state structure of these compounds, a phenomenon that is strongly supported by variable temperature NMR measurements on 2-bromo-6-diisopropylamino-1-azafulvene (3c).Key words: 2-bromo-6-diisopropylamino-1-azafulvenes, stereochemistry, lithiation, pyrolle-2-carboxaldehydes.

Synthesis of 6H-Pyrrolotriazoles and 5H-Pyrrolotetrazoles: Alkylation and Acylation of the Monoanions

Thermal cyclization of 1-azido-2-penten-4-ynes and 4-azido-2-butenenitriles led to 6H-pyrrolotriazoles and 5H-pyrrolotetrazoles, respectively, in good yields.Upon treatment with methyllithium these heterocyclic compounds gave the corr

216. Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6-(Diisopropylamino)-1-azafulvene Derivatives. Novel Synthesis of 5-Mono- and 4,5-Disubstituted 1H-Pyrrole-2-carbaldehydes

The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12.These Li species reacted with sundry electrophilic reagents to give products which, on the basic hydrolysis, were converted into 5-mono- or 4,5-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.

LITHIATION OF THE DIMER OF 3-BROMO-6-DIMETHYLAMINO-1-AZAFULVENE. EFFICACIOUS SYNTHESIS OF 4-MONO- AND 4,5-DISUBSTITUTED PYRROLE-2-CARBOXALDEHYDES.

The dimer 1a of 3-bromo-6-dimethylamino-1-azafulvene, is shown to function as a formal equivalent of 4-lithio- or 4,5-dilithiopyrrole-2-carboxaldehyde and consequently it is a progenitor, par excellence, of 4-mono- and 4,5-disubstituted pyrrole-2-carboxaldehydes.

The interaction of bacterioopsin with 11,14-bridged retinals. The synthesis of 13-demethyl-11,14-imino-, 13-demethyl-N-methyl-11,14-imino-, 13-demethyl-11,14-thio-, 13-demethyl-11,14-etheno-, 11,14-imino-retinal and their binding with bacterioopsin

The synthesis of the all-trans and 9-cis isomers of 11,14-imino-retinal, 13-demethyl-11,14-imino-retinal, 13-demethyl-N-methyl-11,14-imino-retinal, 13-demethyl-11,14-thio-retinal and 13-demethyl-11,14-etheno-retinal is described.The interaction of these retinals with bacterioopsin has been investigated.The all-trans isomers bind to bacterioopsin to form complexes with αmax values around 430 nm.These complexes are stable and do not convert into bacteriorhodopsin analogues.In these complexes the aldehyde group is still present and can be reduced in situ using NaBH4.The fact that these bridged retinals do not form bacteriorhodopsin analogues must be due to the steric hindrance or to the electronic perturbations of the system caused by the bridging group.