10333-67-2

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1003, 1988 DOI: 10.1002/jhet.5570250357The Journal of Organic Chemistry, 27, p. 2466, 1962 DOI: 10.1021/jo01054a042

InChI:InChI=1/C12H15NO2/c1-15-12(14)10-6-2-3-7-11(10)13-8-4-5-9-13/h2-3,6-7H,4-5,8-9H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 635-90-5 1-phenylpyrrole 
• 124-38-9 carbon dioxide 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 134-20-3 2-carbomethoxyaniline 
• 109-97-7 pyrrole 
• 394-35-4 methyl 2-fluorobenzoate 
• 110-16-7 maleic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 7379-35-3 4-chlorpyridine hydrochloride 

Downstream Products

• 87573-97-5 2-(2-Thiocyanato-pyrrol-1-yl)-benzoic acid methyl ester 
• 10333-68-3 1-(2-carboxyphenyl)pyrrole 
• 61034-86-4 2-(pyrrol-1-yl)-benzyl alcohol 
• 31739-63-6 o-(Pyrryl-1-yl)benzohydrazid 
• 79100-16-6 methyl 2-(2-formyl-1H-pyrrol-1-yl)benzenecarboxylate 
• 61034-94-4 2-dimethylaminomethyl-1-(2-methoxycarbonylphenyl)pyrrole 
• 31739-56-7 2-(1H-pyrrol-1-yl)benzaldehyde 
• 1026691-83-7 4-(2-trifluoromethyl-phenylamino)-pyrrolo[1,2-a]quinolin-5-ol 
• 323185-57-5 (+/-)-5,6-dihydro-5-phenyl-4H-pyrrolo[1,2-a][1]benzoxazepin-4-one 
• 323185-56-4 5-phenyl-4H-pyrrolo[1,2-a][1]benzazepin-4-one 
• 323185-54-2 methyl cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamate 
• 323185-55-3 cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamic acid 

Relevant academic research and scientific papers

N-phenylpyrrole: A kinetic, though not thermodynamic preference for dilithiation

Under appropriate conditions the clean preparation of either the α-monolithiated or the o,α-dilithiated derivative of N-phenylpyrrole is possible. In the latter case, the first deprotonation occurs at the α-position. Dimetalation is kinetically but not thermodynamically favored.

Bronsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[ f ]pyrrolo[1,2- a ][1,4]diazepines

Two approaches involving intramolecular and intermolecular cyclization, respectively, have been developed for the direct and practical construction of a series of important benzo[ f ]pyrrolo[1,2- a ][1,4]azepines by using Bronsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2-[2-(1 H -pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[ f ]pyrrolo[1,2- a ][1,4]azepines in high yields. Furthermore, enantioenriched benzo[ f ]pyrrolo[1,2- a ][1,4]azepines were also obtained by chiral phosphoric acid catalyzed intermolecular addition of [2-(1 H -pyrrol-1-yl)phenyl]methanamines to 2-formylbenzoates under mild conditions.

Pd(OAc)2-catalyzed one-pot preparation of anthranilates from acyclic unsaturated β-enamino esters

A one-pot synthesis of anthranilates from acyclic unsaturated β-enamino esters with a catalytic amount of Pd(OAc)2 was achieved for the first time. The substrates for the key catalytic reaction were easily prepared from acetoacetate esters and amines, and functionalized anthranilates were obtained in moderate to good chemical yields. A simple assembly of a 13C-labeled anthranilate was demonstrated by applying this protocol. In addition, bioactive NNI-5 was synthesized using this catalytic process.

MODULAR SYNTHESES OF DISCOIPYRROLE TYPE ALKALOIDS AND ANALOGUES

The present invention relates to methods for preparing a variety of discoipyrrole compounds and analogues using an oxidative cyclisation reaction as one of the steps. The present invention also relates to novel discoipyrrole analogues, pharmaceutical comp

Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

(Chemical Equation Presented). The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps

Efficient synthesis of 9H-pyrrolo[1,2-a]indol-9-one derivatives based on active manganese dioxide promoted intramolecular cyclization

A series of 9H-pyrrolo[1,2-a]indol-9-ones have been prepared via in-situ sequential oxidation of [2-(1H-pyrrol-1-yl)phenyl]methanols promoted by active manganese dioxide. The procedure led to title compounds in good yields under mild conditions, without the need to isolate the intermediate aldehydes.

Reactions of 2-(pyrrol-1-yl)benzyl radicals and related species under flash vacuum pyrolysis conditions

2-(Pyrrol-1-yl)phenoxyl, aminyl, thiophenoxyl and benzyl radicals 2a-2d, respectively, were generated in the gas-phase under flash vacuum pyrolysis conditions. In all cases except the phenoxyl, cyclisation took place providing acceptable synthetic routes to the fused heterocycles 11, 14 and 15, respectively. Only sigmatropic rearrangement products were isolated, in low yields, from the phenoxyl 2a. The pyrrolo[1,2-a]benzimidazole 11 adopts the 1H-tautomer exclusively in chloroform solution. Electrophilic substitution reactions of pyrrolo[2,1-b]benzothiophene 14 were studied, including protonation, deuterium exchange, Vilsmeier formylation and reaction with dimethyl acetylenedicarboxylate. 2-(2,5-Diarylpyrrol-1-yl)thiophenoxyl, phenoxyl and aminyl radicals 23a-f, were also generated in the gas-phase under similar conditions. The thiophenoxyls 23a/b gave extremely complex pyrolysate mixtures in which primary cyclisation products were formed by attack of the radical at the pyrrrole ring and attack at the ipso-, ortho- and meta- positions of the aryl ring. Secondary pyrolysis products were obtained by specific sigmatropic shifts of the N-aryl group. The 2,5-di(thien-2-yl)thiophenoxyl radical 23c gave the pyrrolobenzothiazole 31c as the only cyclisation product in low yield. FVP of the phenoxyl and aminyl radical generators 26d and 26f, respectively, gave 3-arylpyrrolo[1,2-f]phenanthridines 46d and 46f, respectively, by a hydrogen transfer-cyclisation mechanism.

Morita-Baylis-Hillman route to 4H-pyrrolo[1,2-a][1]benzazepine derivatives

A simple method for synthesizing substituted 4H-pyrrolo[1,2-a][1]benzazepines using acid-assisted cyclization of the Morita-Baylis-Hillman adducts of 2-(1H-pyrrol-1-yl)benzaldehydes with methyl acrylate or methyl vinyl ketone as a key step has been developed.

Synthesis of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of pyrroles

A new strategy for the synthesis of condensed hetero- or carbocycles such as pyrroloindoles or fluorenes has been developed that involves the Pd-catalyzed cyclization of readily available N-(2-halobenzyl)pyrroles or their phenyl derivatives. The reaction is proposed to proceed via oxidative addition of benzylic halides to Pd(0) followed by base-assisted C-H bond activation. A broad range of condensed cyclic products could be obtained in good to excellent yields under mild conditions. Copyright

Lewis acid catalyzed synthesis of 4-aminopyrrolo[1,2-a]quinolin-5-ol derivatives from 2-(1-pyrrolyl)benzaldehyde and isocyanides

Reaction of 2-(1-pyrrolyl)benzaldehyde with isocyanides in the presence of a catalytic amount of boron trifluoride diethyl etherate was followed by treatment with acetic anhydride in pyridine to give the corresponding O-acetyl derivatives of 4-alkyl(or ar