Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles.

ABSTRACT: A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation is operationally simple, high-yielding, and displays broad substrate scope.

SUBMITTER: Zhang X

PROVIDER: S-EPMC6152356 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles.

Zhang Xueming X Xu Xianxiu X Zhang Dawei D

Molecules (Basel, Switzerland) 20170707 7

A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation is operationally simple, high-yielding, and displays broad substrate scope. ...[more]

PMID: 28686192

Similar Datasets

Triflic-Acid-Catalyzed Tandem Allylic Substitution-Cyclization Reaction of Alcohols with Thiophenols-Facile Access to Polysubstituted Thiochromans.

Project description:Hitherto inaccessible multisubstituted thiochroman derivatives were constructed via the one-pot reaction of thiophenols with allylic alcohols catalyzed by 0.2 equiv triflic acid under metal-free conditions. A variety of thiochroman derivatives can be obtained by this straightforward protocol that allows the introduction of up to four substituents at various locations on the thiochroman skeleton. Relative conformations of all isolated products were confirmed by NOESY NMR studies, and a stepwise mechanism, proceeding via an allylic substitution-intramolecular cyclization protocol, is proposed on the basis of NMR experiments.

| S-EPMC6645051 | biostudies-literature

(3-Phenyl-isoxazol-5-yl)methanol.

Project description:In the title compound, C(10)H(9)NO(2), the isoxazole and phenyl rings form a dihedral angle of 25.82?(3)°. In the crystal, inter-molecular O-H?O hydrogen bonds link the mol-ecules into ribbons propagating along [001]. The crystal packing is further stabilized by weak C-H?O and C-H?N inter-actions.

| S-EPMC2983723 | biostudies-literature

Enantioselective [2 + 2] cycloaddition of <i>N</i>-allenamides with cyclic <i>N</i>-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters.

Project description:A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).

| S-EPMC5427681 | biostudies-literature

N-{4-[(5-Methyl-isoxazol-3-yl)sulfamo-yl]phen-yl}benzamide.

Project description:In the title compound, C(17)H(15)N(3)O(4)S, the five-membered isoxazole ring makes dihedral angles of 80.5 (2) and 81.3 (2)° with the two benzene rings, which form a dihedral angle of 39.81 (18)° with each other. A short intra-molecular C-H⋯O contact occurs. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which generate [001] chains, and further consolidated by weak C-H⋯O inter-actions.

| S-EPMC3007873 | biostudies-literature

AgNTf2-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives.

Project description:A formal [3 + 2] cycloaddition between ynamides and unprotected isoxazol-5-amines has been developed in the presence of catalytic AgNTf2 in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives can be obtained in up to 99% yield. The reaction mechanism might involve the generation of an unusual ?-imino silver carbene intermediate (or a silver-stabilized carbocation) and subsequent cyclization/isomerization to build the significant pyrrole-3-carboxamide motif. The reaction features the use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatographic purification for most of products and high yields.

| S-EPMC6880818 | biostudies-literature

2-[(E)-(3,4-Dimethyl-isoxazol-5-yl)imino-meth-yl]phenol.

Project description:The title compound, C(12)H(12)N(2)O(2), has been synthesized by the reaction of 5-amino-3,4-dimethyl-isoxazole and salicyladehyde. The mol-ecule adopts an E configuration about the central C=N double bond. The dihedral angle between the isoxazole and phenyl rings is 4.2 (2)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The crystal studied was a non-merohedral twin with a domain ratio of 0.834 (4):0.166 (4).

| S-EPMC2983993 | biostudies-literature

(E)-Benzaldehyde O-{[3-(pyridin-3-yl)isoxazol-5-yl]meth-yl}oxime.

Project description:The asymmetric unit of the title compound, C(16)H(13)N(3)O(2), contains two independent mol-ecules in which the pyridine and benzene rings form dihedral angles of 81.7?(2) and 79.8?(2)°, indicating the twist in the mol-ecules. In the crystal, weak C-H?N inter-actions link mol-ecules into chains along [100].

| S-EPMC3344035 | biostudies-literature

1-[(E)-(3,4-Dimethyl-isoxazol-5-yl)imino-meth-yl]-2-naphthol.

Project description:The title Schiff base compound, C(16)H(14)N(2)O(2), has been synthesized by the reaction of 5-amino-3,4-dimethyl-isoxazole and 2-hydr-oxy-1-naphthaldehyde. The dihedral angle between the isoxazole ring and the napthyl ring system is 3.29?(7)°. The mol-ecule adopts an E configuration about the central C=N double bond. Intra-molecular O-H?N hydrogen bonding generates an S(6) ring motif. In the crystal structure, ?-? inter-actions are observed involving the isoxazole ring and the substituted benzene ring of the naphthyl unit, with centroid-centroid distances of 3.5200?(10)?Å.

| S-EPMC2979054 | biostudies-literature

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

Project description: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.

| S-EPMC4703471 | biostudies-literature

Design, synthesis, in silico and biological evaluations of novel polysubstituted pyrroles as selective acetylcholinesterase inhibitors against Alzheimer's disease.

Project description:The objective of this study was to design new polysubstituted pyrrole derivatives as selective acetylcholinesterase (AChE) inhibitors to target Alzheimer's disease. In this context, a highly efficient, one-pot, sequential, multi-component synthesis of a diverse range of polysubstituted pyrroles was developed through a sequential domino strategy by the condensation of amines with 1,1-bis(methylthio)-2-nitroethene (BMTNE), Knovenagle reaction of arylglyoxals with malono derivatives and subsequent Michael addition and intramolecular cyclization reaction in EtOH at reflux. Thirty-nine synthesized compounds were evaluated as AChE and butyrylcholinesterase (BChE) inhibitors. Among the synthesized compounds, compound 4ad (IC50 = 2.95 ± 1.31 µM) was the most potent and selective AChE inhibitor with no significant inhibition against butyrylcholinesterase BChE. A kinetic study of 4ad revealed that this compound inhibited AChE in an uncompetitive mode. Based on a molecular modeling study, compound 4ad due to its small size properly fitted into the active site of AChE compared to BChE and stabilized by H-bond and hydrophobic interactions with the critical residues of the AChE binding pocket. Consequently, it was proposed that the 4ad derivative can be an ideal lead candidate against AD with a simple and practical operation of synthetic procedures.

| S-EPMC9454393 | 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