Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Atom Economical Multi-Substituted Pyrrole Synthesis from Aziridine.

ABSTRACT: Multi-substituted pyrroles are synthesized from regiospecific aziridine ring-opening and subsequent intramolecular cyclization with a carbonyl group at the γ-position in the presence of Lewis acid or protic acid. This method is highly atom economical where all the atoms of the reactants are incorporated into the final product with the removal of water. This new protocol is applied to the synthesis of various pyrroles, including natural products.

SUBMITTER: Macha L

PROVIDER: S-EPMC9609358 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Atom Economical Multi-Substituted Pyrrole Synthesis from Aziridine.

Macha Lingamurthy L Jala Ranjith R Na Sang-Yun SY Ha Hyun-Joon HJ

Molecules (Basel, Switzerland) 20221013 20

Multi-substituted pyrroles are synthesized from regiospecific aziridine ring-opening and subsequent intramolecular cyclization with a carbonyl group at the <i>γ</i>-position in the presence of Lewis acid or protic acid. This method is highly atom economical where all the atoms of the reactants are incorporated into the final product with the removal of water. This new protocol is applied to the synthesis of various pyrroles, including natural products. ...[more]

PMID: 36296466

Similar Datasets

Atom-Economical and Metal-Free Synthesis of Multisubstituted Furans from Intramolecular Aziridine Ring Opening.

Project description:Multisubstituted furans were prepared from dialkyl 2-(aziridin-2-ylmethylene)malonate and/or 1,3-dione through aziridine ring opening by the internal carbonyl oxygen with the assistance of BF3·OEt2, followed by aromatization. This synthetic method is free from any metal and is atom-economical with all of the atoms in the starting material retained in the final product.

| S-EPMC6645301 | biostudies-literature

A ruthenium-catalyzed, atom-economical synthesis of nitrogen heterocycles.

Project description: Not available

| S-EPMC2888904 | biostudies-literature

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

Project description:A copper triflate-mediated approach to access copper complexes of pyrrole-substituted corroles from the reaction of 1,9-diformyldipyrromethanes and an excess amount of pyrrole is presented for the first time. This procedure is a simple and efficient way for the preparation of corroles with a polymerizable substituent on meso-positions.

| S-EPMC9551205 | biostudies-literature

Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches.

Project description:Of the concepts used to improve the efficiency of organic syntheses, two have been especially effective: atom economy (the use of routes in which most of the atoms present in the reactants also end up in the product) and chemoselectivity (the use of reactions that take place only at desired positions in a molecule). Synthesis of complex natural products is the most demanding arena in which to explore such principles. The bryostatin family of compounds are especially interesting targets, because they combine structural complexity with promising biological activity. Furthermore, synthetic routes to some bryostatins have already been reported, providing a benchmark against which new syntheses can be measured. Here we report a concise total synthesis of bryostatin 16 (1), a parent structure from which almost all other bryostatins could in principle be accessed. Application of atom-economical and chemoselective reactions currently under development provides ready access to polyhydropyran motifs in the molecule, which are common structural features of many other natural products. The most notable transformations are two transition-metal-catalysed reactions. The first is a palladium-catalysed reaction of two different alkynes to form a large ring. The product of this step is then converted into a dihydropyran (the 'C ring' of bryostatins) in the second key reaction, which is catalysed by a gold compound. Analogues of bryostatin that do not exist in nature could be readily made by following this route, which might allow the biological activity of bryostatins to be fine-tuned.

| S-EPMC2728752 | biostudies-literature

Copper-catalyzed reaction of aziridine for the synthesis of substituted imidazolidine and imidazolidinone.

Project description:Herein we report a copper-catalyzed synthesis of imidazolidine by employing the reaction of aziridine with imine. The reaction smoothly provided a diverse range of 2-substituted imidazolidines with high compatibility with various functional groups. Moreover, during our investigation, we discovered that isocyanate also reacted with aziridine to yield substituted imidazolidinones efficiently. The versatility of these reactions was further demonstrated by their application in the synthesis of hybrid molecules derived from two pharmaceutical compounds. This approach opens new possibilities for the discovery of novel classes of bioactive molecules.

| S-EPMC10570437 | biostudies-literature

Zirconium-Catalyzed Atom-Economical Synthesis of 1,1-Diborylalkanes from Terminal and Internal Alkenes.

Project description:A general and atom-economical synthesis of 1,1-diborylalkanes from alkenes and a borane without the need for an additional H2 acceptor is reported for the first time. The key to our success is the use of an earth-abundant zirconium-based catalyst, which allows a balance of self-contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H2 acceptor, which was required in other reported systems. Furthermore, substrates such as simple long-chain aliphatic alkenes that did not react before also underwent 1,1-diboration in our system. Significantly, the unprecedented 1,1-diboration of internal alkenes enabled the preparation of 1,1-diborylalkanes.

| S-EPMC7496309 | biostudies-literature

Heterogeneous Prolinamide-Catalyzed Atom-Economical Synthesis of β-Thioketones from Bio-Based Enones.

Project description:Sulfur-containing compounds are a class of important motifs extensively applied in pharmaceutical and pesticidal industries as well as in electrochemistry, toxicant separation, and organic syntheses. Herein, we describe a novel and efficient metal-free catalytic strategy for the rapid synthesis of β-thioketones from sustainable enone derivatives and thiols via thia-Michael addition enabled by heterogeneous prolinamide. At room temperature, up to 98% yield of β-thioketones could be obtained over the solid UiO-66-NH-proline catalyst facilely prepared by the covalent immobilization of proline onto UiO-66-NH2 (a well-known metal-organic framework) via a stable amido linkage. A cooperative effect of proline (amino group) and UiO-66-NH2 (in situ-derived amide species) was observed to play a promotional role in the proceeding of thia-Michael addition, resulting in a high TOF value of 1124.3 h-1. A three-component "iminium" intermediate was illustrated to the key species approaching the product β-thioketone. Moreover, the UiO-66-NH-proline could be easily recovered from the reaction mixture and recycled for at least five times with a slight loss of activity.

| S-EPMC6545542 | biostudies-literature

Catalytic asymmetric addition of thiols to silyl glyoxylates for synthesis of multi-hetero-atom substituted carbon stereocenters.

Project description:A chiral Lewis acid-catalyzed enantioselective addition of thiols to silyl glyoxylates was developed. The reaction proceeds well with a broad range of thiols and acylsilanes, affording the target tertiary chiral α-silyl-α-sulfydryl alcohols with multi-hetero-atom carbon stereocenters in excellent yields (up to 99%) and enantioselectivities (up to 98% ee). A series of control experiments were conducted to elucidate the reaction mechanism.

| S-EPMC8171345 | biostudies-literature

Atom-Economical Synthesis of <i>N</i>-Arylamides Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts.

Project description:Existing methods for the catalytic synthesis of N-arylamides are limited by a narrow substrate scope, high catalyst costs, and complicated purification processes of products. To overcome these limitations, this study developed an ecofriendly method for the synthesis of N-arylamides using isopropenyl esters. Isopropenyl esters activated using heterogeneous acid catalysts reacted smoothly even with less reactive arylamines to afford N-arylamides in high yields. This method exhibits a wide substrate scope and is applicable for the synthesis of various N-arylamides (33 examples, 46-99% yield). The developed method enabled the obtainment of high-purity products with a facile workup procedure and showed excellent process mass intensity values due to the reduction of chemical waste.

| S-EPMC10688214 | biostudies-literature

Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin.

Project description:A convenient and efficient one-step synthesis of 1,1,1-triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)2 . This process proceeds under mild conditions, furnishing 1,1,1-tris(boronates) with wide substrate scope, excellent selectivity, and good functional-group tolerance, and is applicable to gram-scale synthesis without loss of yield. The 1,1,1-triborylalkanes can be used in the preparation of α-vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base-mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols.

| S-EPMC6972527 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data