Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

'One-pot' synthesis of dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a silver(I)-catalyzed cascade approach.

ABSTRACT: An efficient approach for the synthesis of biologically interesting fused tetracyclic isoquinolines in high yields and with a broad substrate scope has been developed. The strategy features an AgNO(3) catalyzed 'one-pot' cascade process involving formation of two new C-N bonds and one new C-O bond.

SUBMITTER: Jiang B

PROVIDER: S-EPMC6270568 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

'One-pot' synthesis of dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a silver(I)-catalyzed cascade approach.

Jiang Baifeng B Zhou Yu Y Kong Qingya Q Jiang Hualiang H Liu Hong H Li Jian J

Molecules (Basel, Switzerland) 20130111 1

An efficient approach for the synthesis of biologically interesting fused tetracyclic isoquinolines in high yields and with a broad substrate scope has been developed. The strategy features an AgNO(3) catalyzed 'one-pot' cascade process involving formation of two new C-N bonds and one new C-O bond. ...[more]

PMID: 23344195

Similar Datasets

Synthesis of 2-trifluoromethylpyrazolo[5,1-a]isoquinolines via silver triflate-catalyzed or electrophile-mediated one-pot tandem reaction.

Project description:An efficient one-pot tandem cyclization/[3 + 2] cycloaddition reaction of N'-(2-alkynylbenzylidene)hydrazides with ethyl 4,4,4-trifluorobut-2-ynoate under silver triflate-catalyzed or electrophile-mediated conditions is described. Various trifluoromethylated pyrazolo[5,1-a]isoquinolines were afforded in moderate to excellent yield by this developed method.

| S-EPMC4187034 | biostudies-literature

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines.

Project description:The development of a general method utilizing a hydroxymethyl directing group for asymmetric hydrogenation of 1,3-disubstituted isoquinolines to provide chiral 1,2,3,4-tetrahydroisoquinolines is reported. The reaction, which utilizes [Ir(cod)Cl]2 and a commercially available chiral xyliphos ligand, proceeds in good yield with high levels of enantioselectivity and diastereo-selectivity (up to 95% ee and >20:1 dr) on a range of differentially substituted isoquinolines. Directing group studies demonstrate that the hydroxymethyl functional group at the C1-position is more efficient at enabling hydrogenation than other substituents, although high levels of enantioselectivity were conserved across a variety of polar and non-polar functional groups. By utilizing the generated chiral β-amino alcohol as a functional handle, the synthetic utility is further highlighted via the synthesis of 1,2-fused oxazolidine, oxazolidinone, and morpholinone tetrahydroisoquinolines in one step. Additionally, a non-natural analog of the tetrahydroprotoberberine alkaloids was successfully synthesized.

| S-EPMC8152574 | biostudies-literature

Lewis Acid-Catalyzed Vinyl Acetal Rearrangement of 4,5-Dihydro-1,3-dioxepines: Stereoselective Synthesis of <i>cis-</i> and <i>trans-</i>2,3-Disubstituted Tetrahydrofurans.

Project description:Lewis acid-catalyzed rearrangements of 4,5-dihydro-1,3-dioxepines have been investigated. Rearrangement of vinyl acetals under a variety of conditions resulted in cis- and trans-2,3-disubstituted tetrahydrofuran derivatives in a highly stereoselective manner. Rearrangements at lower temperatures typically provided the cis-2,3-disubstituted tetrahydrofuran carbaldehydes. At higher temperatures, the corresponding trans-2,3-disubstituted tetrahydrofuran carbaldehydes are formed. The requisite substrates for the vinyl acetal rearrangement were synthesized via ring-closing olefin metathesis of bis(allyoxy)methyl derivatives using Grubbs second-generation catalyst followed by olefin isomerization using a catalytic amount of RuCl2(PPh3)3. We examined the substrate scope using substituted aromatic and aliphatic derivatives. Additionally, the rearrangement was utilized in the synthesis of a stereochemically-defined bis-tetrahydrofuran (bis-THF) derivative, which is one of the key structural elements of darunavir, an FDA-approved drug for the treatment of HIV/AIDS.

| S-EPMC7898272 | biostudies-literature

One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.

Project description:Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.

| S-EPMC6933537 | biostudies-literature

Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.

Project description:Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3-enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(i)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.

| S-EPMC6839590 | biostudies-literature

Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3,4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors.

Project description:Poly(ADP-ribose) polymerase 1 (PARP1), a widely explored anticancer drug target, plays an important role in single-strand DNA break repair processes. High-throughput virtual screening (HTVS) of a Maybridge small molecule library using the PARP1-benzimidazole-4-carboxamide co-crystal structure and pharmacophore model led to the identification of eleven compounds. These compounds were evaluated using recombinant PARP1 enzyme assay that resulted in the acquisition of three PARP1 inhibitors: 3 (IC50 = 12 μM), 4 (IC50 = 5.8 μM), and 10 (IC50 = 0.88 μM). Compound 4 (2,3-dihydro-1,4-benzodioxine-5-carboxamide) was selected as a lead and was subjected to further chemical modifications, involving analogue synthesis and scaffold hopping. These efforts led to the identification of (Z)-2-(4-hydroxybenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide (49, IC50 = 0.082 μM) as the most potent inhibitor of PARP1 from the series.

| S-EPMC8142146 | biostudies-literature

1,1-Bis(4-fluoro-phen-yl)-3,4-dihydro-1H-1,3-oxazino[3,4-a]indole.

Project description:The title compound, C(23)H(17)F(2)NO, which crystallizes with two independent mol-ecules in the asymmetric unit, was prepared by the cyclization of 4-[2-bis-(4-fluoro-phen-yl)methyl-eneamino]but-3-yn-1-ol at room temperature. The mol-ecules display a tripod conformation. The two fluoro-phenyl rings make dihedral angles of 79.26?(2) and 85.87?(1)° [86.53?(1) and 83.67?(2)° in the second mol-ecule] with the indole ring, and the dihedral angles between the fluoro-phenyl rings are 67.74?(2) and 66.33?(2)°, respectively. Furthermore, the indole rings are located on the edge of the respective oxazine half-chair ring systems. Nonconventional C-H?? contacts between indole and fluoro-phenyl rings are observed.

| S-EPMC2959698 | biostudies-literature

2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho-[2,3-e][1,4]dithiine-5,10-dione.

Project description:The title mol-ecule, C(13)H(4)O(2)S(5), is folded by 47.83?(6)° along the S?S vector of the [1,4]dithiine six-membered ring, with the naphtho-quinone and [1,3]dithiole-2-thione moieties being nearly planar [largest deviations from least-squares planes = 0.028?(2) and 0.016?(1)?Å, respectively]. This boat conformation is close to that observed in the analogous compound [Mendez-Rojas et al. (2001). J. Chem. Crystallogr.31, 17-28] including a 2-oxo group [folding angle: 42.3?(1)° at 213?(2)?K]. Both compounds are indeed isomorphous, and the small difference in the folding angle probably results from the involvement of the thioxo group of the title compound in inter-molecular S?S contacts [3.5761?(13)?Å]. In the crystal structure, mol-ecules are stacked in the [100] direction, with dithiole rings making ?-? inter-actions. In a stack, alternating short and long separations are observed between the centroids of dithiole rings, 3.5254?(17) and 4.7010?(18)?Å.

| S-EPMC3247576 | biostudies-other

One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of Diazepines Involving Copper-Catalyzed Rearrangement Cascade Allyl-Amination.

Project description:A novel and efficient method has been proposed for the synthesis of 1,4-benzodiazepine-5-ones from o-nitrobenzoic N-allylamides by using molybdenyl acetylacetonate and copper(II) trifluoromethanesulfonate as catalysts in the presence of triphenylphosphine. This synthesis process involves nitrene formation, C-H bond insertion, C═C bond rearrangement, and C-N bond formation cascade reactions via copper- and molybdenum-catalyzed mediation. The method features a wide substrate scope and a moderate to high yield (up to 90%), exhibiting the possibility for practical applications.

| S-EPMC8567460 | biostudies-literature

Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.

Project description:Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.

| S-EPMC2835628 | 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