63122-43-0

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General Description

2-(furan-2-yl)-1H-pyrrole, also known as furanopyrrole, is a chemical compound with a molecular formula C9H7NO. It is a heterocyclic aromatic compound containing a pyrrole ring fused with a furan ring. 2-(furan-2-yl)-1H-pyrrole is commonly used in organic synthesis and pharmaceutical research as a building block for various organic compounds. It has been the subject of research for its potential medicinal properties, particularly in the field of anti-cancer and anti-inflammatory drug development. Furanopyrrole is also known for its unique electronic and optical properties, making it a valuable component in the development of organic electronic materials and optoelectronic devices.

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 1450-49-3 (E)-1-(furan-2-yl)ethanone oxime 
• 74-86-2 acetylene 
• 56139-61-8 4-(2-furyl)-4-oxobutanal 
• 614-99-3 Ethyl 2-furoate 
• 5007-50-1 1-(2-furyl)ethanone oxime 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 140484-06-6 1,1-dimethoxy-4-(2-furyl)-4-butanone 
• 611-13-2 2-furoic acid methyl ester 
• 63122-36-1 N-allylfuran-2-carboxylic acid amide 
• 527-69-5 2-furancarbonyl chloride 
• 79892-12-9 2-(2-furyl)-1-vinylpyrrole 
• 85868-22-0 O-(2-vinyl) methyl 2-furyl ketoxime 
• 63122-39-4 N-allyl-furan-2-carboximidoyl chloride 

Relevant academic research and scientific papers

Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.

Synthesis and optical properties of 2-(Benzo[b]thiophene-3-yl)pyrroles and a new bodipy fluorophore (BODIPY = 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene)

2-(Benzo[b]thiophene-3-yl)-1-vinylpyrrole has been synthesized directly from 3-acetylbenzo[b]thiophene oxime and acetylene (flow system, KOH-DMSO, 120 °C, 5 h) in 68% yield. Devinylation of the synthesized pyrrole (Hg(OAc)CU2, NaBH4, 50 °C) led to the corresponding 2-(benzo[b]thio-phene-3-yl)pyrrole in 63% yield. Tri-fluoroacetylation of both the pyrroles with trifluoroacetic anhydride (80 °C, 1 h) gave the corresponding 5-trifluor-oacetyl pyrroles in 97% and 76% yields, respectively. 2-(Benzo[b]thio-phene-3-yl)pyrrole was reacted subsequently with mesityl aldehyde, 2,3-di-chloro-5,6-dicyano-1,4-benzoquinone (DDQ), and BF 3·OEt2 to afford 4,4-di-fluoro-3,5- diT(benzo[CAGHRUENb]thiophene-3-yl)-8-mesityl-4-bora-3a,4a-diaza-s-inda-cene, a representative of the novel BODIPY fluorophore family (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), in 34% overall yield. The synthesized pyrroles exhibit promising optical properties (absorption and emission spectra, nonlinear optical (NLO) features), superior to existing analogues. The BODIPY fluorophore displays an intense red-shifted fluorescence emission in CH2Cl2(625 nm, 0.84 fluorescence quantum yield) that is fully preserved in the solid state.

The triphenyl phosphite-chlorine reagent in the synthesis of pyrroles from N-allylamides

A novel application of (PhO)3P-Cl2 chemistry to the synthesis of 2-substituted and 2,3-disubstituted pyrroles from N-allyl-amides is illustrated. A mild procedure is used to generate the imino chloride intermediates, which are subseq

Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction

Substituted pyrroles were prepared by a gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides. The reaction allows for regiospecific substitution at each position of the pyrrole ring under mild conditions. A mechanism in which azides serve as nucleophiles toward gold(I)-activated alkynes with subsequent gold(I)-aided expulsion of dinitrogen is proposed. Copyright

A second generation synthesis of roseophilin and chromophore analogues

A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl2(PCy3)2Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschlorodesmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.

N-Vinyl Pyrroles as Protected Pyrroles

N-Vinyl-2-phenyl-, N-vinyl-3-isopropyl-2-(4-methoxyphenyl)-, N-vinyl-3-isopropyl-2-(4-chlorophenyl)-, N-vinyl-2-furyl-, N-vinyl-2-(5-methyl-2-furyl)pyrroles were converted into N-unsubstituted pyrroles in 67-99% yield by mercuration with mercury(II) acetate with subsequent reduction of the intermediate with sodium borohydride. An exception was N-vinyl-3-isopropyl-2-(4-chlorophenyl)pyrrole which gave the corresponding N-unsubstituted pyrrole in as low as 38% yield.

NUCLEOPHILIC ADDITION TO ALKYNES IN SUPERBASIC CATALYTIC SYSTEMS. V. VINYLATION OF KETOXIMES

The nucleophilic addition of the oximes of aliphatic, aromatic, and heteroaromatic ketones to acetylene in the superbasic heterophase potassium hydroxide-DMSO system was studied.The vinylation of ketoximes not containing a CH2 group at the α position to the oxime function goes well, and the yields of the O-vinyloximes are 38-72percent.With such a group and with electronegative substituents in the aromatic ring of the ketoxime rapid heterocyclization of the O-vinyloximes occurs under the reaction conditions, giving the corresponding 2-substituted pyrroles.

CONVENIENT METHOD OF PREPARING 3-SUBSTITUTED 2,2'-FURYL(THIENYL)PYRROLES

2,2'-Furyl(thienyl)pyrroles and their 3-decylthio derivatives were synthesized by the Paal-Knorr reaction from the corresponding 3-unsubstituted or 3-decylthio-substituted dimethylacetals of 4-(2-furyl)- and 4-(2-thienyl)-4-oxobutanal.The starting materia

PYRROLES ROM KETOXIMES AND ACETYLENE. 40. REACTION OF ALKYL HETARYL KETOXIMES WITH 1,2-DICHLOROETHANE IN SUPERBASE MEDIA

2-(2-Furyl)- and 2-(2-thienyl)pyrroles and their N-vinyl derivatives were synthesized by the reaction of alkyl furyl (thienyl) ketoximes with 1,2-dichloroethane in superbase media. 2-Chloroethyl and vinyl ethers of alkyl hetaryl ketoximes are intermediates in the reaction.

Silylamines in organic synthesis: preparation and some reactions of N,C-dilithiosilylamines

The dimetallation of some olefinic and aromatic N-trimethylsilylamines has been examined.Treatment with a two molar proportion of n-butyllithium gives organodimetallic reagents, which react with trimethylchlorosilane to give N,N,C-tris(trimethylsilyl)amines in 45 to 65percent yields.The dianonic reagent obtained from (trimethylsilyl)(allyl)amine reacts with benzoyl chloride, N,N-dimethylformamide, ethyl-2-furylcarboxylate, and benzil to give substituted pyrroles and pyridines.