Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles.

ABSTRACT: A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels-Alder reaction sequence, resulting in continuous multiple bond-forming events including C-N, C-O and C-H bonds to rapidly build up molecular complexity.

SUBMITTER: Gao Q

PROVIDER: S-EPMC4703471 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles.

Gao Qian Q Hao Wen-Juan WJ Liu Feng F Tu Shu-Jiang SJ Wang Shu-Liang SL Li Guigen G Jiang Bo B

Chemical communications (Cambridge, England) 20160101 5

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels-Alder reaction sequence, resulting in continuous multiple bond-forming events including C-N, C-O and C-H bonds to rapidly build up molecular ...[more]

PMID: 26576646

Similar Datasets

New Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-<i>d</i>]thiazolo[3,2-<i>a</i>]pyrimidines.

Project description:A novel three-component bicyclization for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines has been established from readily accessible aryl aldehydes, α-thiocyanate ketones and pyrazol-5-amines. The reaction pathway involves nucleophilic addition/5-exo-trig /6-endo-trig bicyclization sequence, resulting in continuous multiple bond-forming events including C-N and C-C bonds to rapidly a molecular complexity.

| S-EPMC5489242 | biostudies-literature

Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion.

Project description:A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.

| S-EPMC7011176 | biostudies-literature

Four-component bicyclization approaches to skeletally diverse pyrazolo[3,4-b]pyridine derivatives.

Project description:A novel four-component bicyclization strategy has been established, allowing a flexible and practical approach to 37 examples of multicyclic pyrazolo[3,4-b]pyridines from low-cost and readily accessible arylglyoxals, pyrazol-5-amines, aromatic amines, 4-hydroxy-6-methyl-2H-pyran-2-one, and cyclohexane-1,3-diones. The polysubstituted cyclopenta[d]pyrazolo[3,4-b]pyridines were stereoselectively synthesized through a microwave-assisted special [3+2+1]/[3+2] bicyclization with good control of the spatial configuration of exocyclic double bonds. The novel [3+2+1]/[2+2+1] bicyclization resulted in 17 examples of unreported pyrazolo[3,4-b]pyrrolo[4,3,2-de]quinolones. Reasonable mechanisms for forming two new types of multicyclic pyrazolo[3,4-b]pyridines are also proposed.

| S-EPMC4242041 | biostudies-literature

Stereoselective Four-Component Synthesis of Functionalized 2,3-Dihydro-4-Nitropyrroles.

Project description:We report a metal-free and stereoselective four-component reaction between ?-ketoamides, amines, aromatic aldehydes and ?-nitroalkenes or ?-pivaloxy-nitroalkanes to obtain 2,3-dihydro-4-nitropyrroles functionalized in every position. The heterocycles accessible using this reaction may have utility in the synthesis of pharmacologically active compounds.

| S-EPMC6988783 | biostudies-literature

Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.

Project description:In the presence of triethylamine as catalyst, the one-pot four-component reactions of arylamines, methyl propiolate, isatin and malononitrile afforded the functionalized spiro[indoline-3,4'-pyridine] derivatives in good yields. Similar reactions with ethyl cyanoacetate successfully afforded the functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] as the main products according to the structures of the arylamines and other primary amines.

| S-EPMC3678513 | biostudies-literature

Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions.

Project description:Reaction of benzimidazolone derivatives, or their thio- or aza-counterparts, with an isocyanide in the presence of acetone unexpectedly gave rise to novel tricyclic benzodiazepine derivatives in good yield by means of a four-component reaction incorporating two moles of acetone. Benzimidazole starting substrates bearing an electron-withdrawing group gave rise instead to dihydroquinoxaline derivatives by means of a three-component reaction. Use of deuterated acetone instead of acetone in the reactions significantly affected yield and reactivity in the four-component reaction but not in the three-component reaction.

| S-EPMC9036818 | biostudies-literature

Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles.

Project description:The synthesis of N-acyl 3,4-disubstituted pyrroles can be accomplished directly from hydrazine and an aldehyde via a Piloty-Robinson pyrrole synthesis. The use of microwave radiation for the cyclization and pyrrole formation greatly reduces the time necessary for this process and facilitates moderate to good yields from hydrazine for the corresponding 3,4-disubstituted products (5-12). By simple hydrolysis, the free N-H pyrroles can be accessed after the Piloty-Robinson reaction and then used directly in the synthesis of octaethylporphyrin (H2OEP, 14) and octaethyltetraphenylporphyrin (H2OETPP, 15).

| S-EPMC1939979 | biostudies-literature

3,4-Dimethyl-pyrano[2,3-c]pyrazol-6(2H)-one.

Project description:The asymmetric unit of the title compound, C(8)H(8)N(2)O(2), comprises two independent mol-ecules in both of which, all non-H atoms lie in a common plane (r.m.s. deviation = 0.014 and 0.017?Å). In the crystal, N-H?O hydrogen bonds connect the mol-ecules into zigzag chains running along [10-1]. Weak C-H?O inter-actions connect the chains into an infinite network.

| S-EPMC3344151 | biostudies-literature

Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Project description:We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the α-carboxamido lactone - into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

| S-EPMC5347843 | biostudies-literature

One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines].

Project description:The one-pot four-component reaction of benzohydrazide (2-picolinohydrazide), acetylenedicarboxylate, isatins and malononitrile (ethyl cyanoacetate) with triethylamine as base catalyst afforded functionalized 1-benzamidospiro[indoline-3,4'-pyridines] in good yields. (1)H NMR spectra indicated that an equilibrium of cis/trans-conformations exist in the obtained products.

| S-EPMC4273213 | 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