Synthesis Of Pyrrolo Research Articles

PIFA-Mediated oxidative cyclization of 1-aroyl-N-arylcyclopropane-1-carboxamides and their application in the synthesis of pyrrolo[3,2-c]quinolinones

A PIFA-promoted ring-closing reaction for the synthesis of spirocyclopropane quinolinediones, and their application toward pyrrolo[3,2-c]quinolinones.

ChemInform Abstract: Synthesis of Pyrrolo[1,2‐a]quinolines and Ullazines by Visible Light Mediated One‐ and Twofold Annulation of N‐Arylpyrroles with Arylalkynes.

AbstractThe annulation of N‐(2‐bromophenyl)pyrroles (I) with arylalkynes (II) gives rise to desired pyrrolo[1,2‐a]quinolines (III).

ChemInform Abstract: An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines

AbstractReview: 100 refs.

Synthesis of Pyrrolo[2,3-d]pyrimidines by Copper-Mediated Carbomagnesiations of N-Sulfonyl Ynamides and Application to the Preparation of Rigidin A and a 7-Azaserotonin Derivative.

The treatment of readily available N-alkynyl-5-iodo-6-sulfamido-pyrimidines with iPrMgCl⋅LiCl followed by a transmetalation with CuCN⋅2 LiCl produces, after intramolecular carbocupration, metalated pyrrolo[2,3-d]pyrimidines. Quenching of these pyrimidines with allylic halides or acid chlorides results in polyfunctional pyrrolo[2,3-d]pyrimidines. Further reaction with ICl and a Negishi cross-coupling, using PEPPSI-iPr as the catalyst, furnishes fully substituted N-heterocycles. A formal synthesis of the marine alkaloid rigidin A has been achieved as well as the preparation of a derivative of 7-azaserotonine, related to the natural hormone serotonin.

One-Pot, Green and Efficient Synthesis of Pyrrolo[1,2-α]Quinoxalines in Water

A variety of pyrrolo[1,2-α]quinoxaline derivatives were synthesised via the reaction of 1,2-diamines with dibenzoylacetylene and dialkyl acetylenedicarboxylates in the presence of ethyl bromopyruvate in water. This novel, eco-friendly approach offers an easy, efficient, and mild synthesis of pyrrolo[1,2-α]quinoxaline derivatives in good yields.

Annulation Reaction of 3-Acylmethylidene Oxindoles with Huisgen Zwitterions and Its Applications in the Syntheses of Pyrrolo[4,3,2-de]quinolinones and Marine Alkaloids Ammosamides.

A novel annulation reaction of 3-acylmethylidene oxindoles with Huisgen zwitterions is unveiled that leads to an unprecedented synthetic method for complex pyrrolo[4,3,2-de]quinolinones and marine alkaloids ammosamides A-C. This method features simplicity, high efficiency, and broad substrate scope and is accordingly anticipated to significantly facilitate the preparation and bioassay of the relevant pyrroloquinoline alkaloids and their analogues.

An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines.

Pyrrolo[1,4]benzodiazepines are tricyclic compounds that are considered “privileged structures” since they possess a wide range of biological activities. The first encounter with these molecules was the isolation of anthramycin from cultures of Streptomyces, followed by determination of the X-ray crystal structure of the molecule and a study of its interaction with DNA. This opened up an intensive synthetic and biological study of the pyrrolo[2,1-c][1,4]benzodiazepines that has culminated in the development of the dimer SJG-136, at present in Phase II clinical trials. The synthetic efforts have brought to light some new synthetic methodology, while the contemporary work is focused on building trimeric pyrrolo[2,1-c][1,4]benzodiazepines linked together by various heterocyclic and aliphatic chains. It is the broad spectrum of biological activities of pyrrolo[1,2-a][1,4]benzodiazepines that has maintained the interest of researchers to date whereas several derivatives of the even less studied pyrrolo[1,2-d][1,4]benzodiazepines were found to be potent non-nucleoside HIV-1 reverse transcriptase inhibitors. The present review is an update on the synthesis of pyrrolo[2,1-c][1,4]benzodiazepines since the last major review of 2011, while the overview of the synthesis of the other two tricyclic isomers is comprehensive.

Ligand-free Cu-catalyzed [3 + 2] cyclization for the synthesis of pyrrolo[1,2-a]quinolines with ambient air as a terminal oxidant.

A ligand-free Cu-catalyzed [3 + 2] cycloaddition of ethyl 2-(quinolin-2-yl)acetates, ethyl 2-(isoquinolin-1-yl)acetates, and ethyl 2-(pyridin-2-yl)acetates with (E)-chalcones for a "one-pot" synthesis of pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines and indolizines has been developed. The annulation products were isolated in moderate to good yields with air as the sole oxidant under mild conditions.

Design and Synthesis of Pyrrolo[2,1-a]Isoquinoline-Based Derivatives as New Cytotoxic Agents.

A new series of anti-cancer agents based on 1,2-diaryl-5,6-dihydropyrrolo[2,1-a]isoquinoline scaffold containing N,N-diethylamino-ethoxy, piperidinyl-ethoxy or morpholinyl-ethoxy group at the para position of the C-2 phenyl ring were synthesized and their cytotoxic activities were assessed against several human cancer cell lines including MCF-7 (ER positive breast cancer cell), MDA-MB231 (ER-negative breast cancer cell), T47D (Human ductal breast epithelial tumor cell line), A549 (adenocarcinomic human alveolar basal epithelial cells), and Hela (human cervix adenocarcinoma cells) using MTT assay. Based on results, compounds, 1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline (6a) and 2-(4-(5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a] isoquinolin-1-yl)phenoxy)-N,N-diethylethanamine (6c) were the most potent cytotoxic compounds and more toxic than the reference compound against T47D cell line, while all the compounds had satisfactory activity against HeLa cell line with mean IC50 values ranging from 1.93 to 33.84 µM.

Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes.

1-(2-Bromophenyl)-1H-pyrrole and 1-(2,6-dibromophenyl)-1H-pyrrole react in the presence of catalytic amounts of rhodamine 6G () and N,N-diisopropylethylamine (DIPEA) under blue light irradiation with aromatic alkynes and subsequently cyclize intramolecularly to form pyrrolo[1,2-a]quinoline and ullazines. The reactions proceed at room temperature, avoid transition metal catalysts, and provide the target compounds in one pot in moderate to good yields. Mechanistic investigations suggest that the photo excited is reduced by DIPEA to form the corresponding radical anion , which is again excited by 455 nm light. The excited radical anion of donates an electron to the aryl bromide giving an aryl radical that is trapped by aromatic alkynes. The intermediate vinyl radical cyclizes intramolecularly and yields the product after rearomatization.

Correction: Insights into the unexpected chemoselectivity in Brønsted acid catalyzed cyclization of isatins with enaminones: convenient synthesis of pyrrolo[3,4-c]quinolin-1-ones and spirooxindoles

Correction for 'Insights into the unexpected chemoselectivity in Brønsted acid catalyzed cyclization of isatins with enaminones: convenient synthesis of pyrrolo[3,4-c]quinolin-1-ones and spirooxindoles' by Hui Xu et al., Chem. Commun., 2016, 52, 8002-8005.

ChemInform Abstract: Preparation of Novel Pyrrolo[2,3‐b]pyridine Derivatives via a New Concise Synthetic Approach.

AbstractA new, concise, three‐step synthesis of pyrrolo[2,3‐b]pyridines is reported starting from L‐alanine.

ChemInform Abstract: Synthesis of Pyrrolo[2,1,5‐cd]indolizines Through Dehydrogenative Heck Annelation of Indolizines with Diaryl Acetylenes Using Dioxygen as an Oxidant.

AbstractThe reaction is restricted to diarylacetylenes (II), (XIII), and (XV).

ChemInform Abstract: Synthesis of Pyrrolo[2,3‐b]pyrazines Through Sonogashira Coupling Reaction of 5,6‐Dichloropyrazine‐2,3‐dicarbonitrile with Hydrazine, Phenylacetylene and Various Aldehydes.

ChemInform Abstract: Synthesis of Pyrrolo[2,3‐b]pyrazines Through Sonogashira Coupling Reaction of 5,6‐Dichloropyrazine‐2,3‐dicarbonitrile with Hydrazine, Phenylacetylene and Various Aldehydes.

Preparation of Novel Pyrrolo[2,3‐b]pyridine Derivatives via a New Concise Synthetic Approach

The pyrrolo[2,3‐b]pyridine core structure, a bioisostere of quinolones, is found in several molecules that possess important biological activity. We describe here a new, concise, three‐step synthesis of pyrrolo[2,3‐b]pyridines starting from L‐alanine. A series of 4,7‐dihydro‐4‐oxo‐1H‐pyrrolo[2,3‐b]pyridine‐5‐carboxylic acid derivatives, which have not been previously reported, were synthesized using this approach.

Synthesis of pyrrolo[2,1,5-cd]indolizines through dehydrogenative Heck annelation of indolizines with diaryl acetylenes using dioxygen as an oxidant.

A dehydrogenative Heck annelation reaction of indolizine with diaryl acetylene via dual C-H bond cleavage was developed. Oxygen gas was employed as a clean oxidant in this catalysis under base-free conditions. Diarylpyrrolo[2,1,5-cd]indolizines were synthesized with high atom economy. In addition, kinetic isotope experiments provided evidence for C-H bond metalation of the 5-position of the indolizine as the rate-limiting step.

A One-Pot Four-Component synthesis of Pyrrolo[1,2-A]Quinolines

A facile one-pot, four-component reaction for the synthesis of pyrrolo[1,2- a]quinolines is described. Knoevenagel condensation reaction of malononitrile and aromatic aldehydes gave 2-arylmethylidenemalononitriles which on treatment with quinoline and cyclohexyl isocyanide under solvent-free conditions afforded 1-(cyclohexylamino)-2-arylpyrrolo[1,2- a]quinoline-3-carbonitriles in good yields.

Synthesis of Pyrrolo[3,2-b]carbazole Derivatives via Palladium-Catalyzed C–H Activation

A simple method for the synthesis of different pyrrolo[3,2-<i>b</i>]carbazole derivatives by the reaction of 3-(acetylamino)carbazoles with various symmetrical diaryl-substituted alkynes via palladium-catalyzed C–H activation is reported.

ChemInform Abstract: One‐Pot Synthesis of Pyrrolo[1,2‐a]pyrazines via Three Component Reaction of Ethylenediamine, Acetylenic Esters and Nitrostyrene Derivatives.

Abstract An effective route to pyrrolo[1,2- a ]pyrazines is described via reaction of ethylenediamine, acetylenic esters and nitrostyrene derivatives in the presence of 20 mol% of sulfamic acid.

Fast and Green One-Pot Multicomponent Synthesis of a Library of Pyrrolo[1,2-c] Pyrimidines Under Microwave Irradiation

A simple, clean and rapid one-pot three component, microwave-assisted synthesis of pyrrolo[1,2-c]pyrimidine derivatives starting from various substituted pyrimidines, 2-bromoacetophenones and nonsymmetrical, electron deficient alkynes in 1,2-epoxybutane which acts both as solvent and acid scavenger is reported. This one-pot three component synthesis implies short reaction times being at the same time highly cost-effective and environmental friendly.