Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

ABSTRACT: Reaction of 6-methyl-1-phenylhept-3-yne-2,6-diol with various aldehydes under Lewis acid conditions provides an atom economical, two-component cascade reaction sequence to novel 2,4-dihydro-1H-benzo[f]isochromene compounds. Aliphatic aldehydes as well as electron-deficient and -rich aromatic aldehydes can be used.

SUBMITTER: Hinkle RJ

PROVIDER: S-EPMC4447333 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

Hinkle Robert J RJ Lewis Shane E SE

Organic letters 20130801 16

Reaction of 6-methyl-1-phenylhept-3-yne-2,6-diol with various aldehydes under Lewis acid conditions provides an atom economical, two-component cascade reaction sequence to novel 2,4-dihydro-1H-benzo[f]isochromene compounds. Aliphatic aldehydes as well as electron-deficient and -rich aromatic aldehydes can be used. ...[more]

PMID: 23901903

Similar Datasets

5-Ethyl-4a-meth-oxy-1,3-dimethyl-4a,5-dihydro-benzo[g]pteridine-2,4(1H,3H)dione.

Project description:The title compound, C(15)H(18)N(4)O(3), was formed by the reaction of methanol with 5-ethyl-1,3-dimethyl-alloxazinium perchlorate. Its structure mimics those of possible flavin inter-mediates in flavoenzymes. The heterocyclic rings are substituted with methyl, ethyl and meth-oxy groups. The central tricyclic skeleton is bent due to the presence of an sp(3) C atom. There are weak inter-molecular C-H?O inter-actions in the structure, forming a three-dimensional network.

| S-EPMC2969355 | biostudies-literature

One-pot synthesis of novel 2,3-dihydro-1H-indazoles.

Project description:A copper(I)-mediated one-pot synthesis of 2,3-dihydro-1H-indazole heterocycles has been developed. This synthetic route provides the desired indazoles in moderate to good yields (55%-72%) which are substantially better than those achievable with an alternative two-step reaction sequence. The reaction is tolerant of functionality on the aromatic ring.

| S-EPMC6264256 | biostudies-literature

2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate.

Project description:In the title compound, C(11)H(10)Br(2)O(2), the cyclo-pentene ring fused to the benzene ring adopts an envelope conformation, with the C atom attached to the Br atom as the flap. The crystal structure does not exhibit any classical hydrogen bonds. The mol-ecular packing is stabilized by van der Waals forces and ?-? stacking inter-actions with a centroid-centroid distance of 3.811?(4)?Å.

| S-EPMC3379444 | biostudies-literature

3-(4-Pyrid-yl)-4,5-dihydro-1H-benzo[g]indazole.

Project description:In the mol-ecular structure of the title compound, C(16)H(13)N(3), the cyclo-hexa-1,3-diene ring displays a screw-boat conformation and the pyridine ring is twisted by a dihedral angle of 29.13?(9)° with respect to the pyrazole ring. Mol-ecules are linked into a supra-molecular structure by N-H?N hydrogen bonding.

| S-EPMC2960070 | biostudies-literature

2,4-Bis(4-fluoro-phen-yl)-2,3-dihydro-1H-1,5-benzodiazepine.

Project description:In the title compound, C(21)H(16)F(2)N(2), the seven-membered 1,4-diazepine ring of the benzodiazepine ring system adopts a distorted-boat conformation. The benzene ring of this system makes dihedral angles of 18.6?(2) and 78.8?(2)° with those of two fluoro-phenyl substituents. In the crystal, inversion dimers linked by two weak C-H?F hydrogen bonds generate R(2) (2)(20) ring motifs. There are also weak N-H?? and C-H?? inter-actions.

| S-EPMC3089231 | biostudies-literature

1-{[(2,3-Dihydro-1H-inden-2-yl)-oxy]meth-yl}quinazoline-2,4(1H,3H)-dione.

Project description:In the title mol-ecule, C(18)H(16)N(2)O(3), the five-membered ring has an envelope conformation, with the substituted C atom deviating by 0.342?(4)?Å from the mean plane P calculated for the remainder of the non-H atoms of the 2,3-dihydro-1H-indene fragment. The mean planes of quinazoline-2,4(1H,3H)-dione fragment and P form a dihedral angle of 59.08?(4)°. In the crystal, pairs of N-H?O hydrogen bonds link mol-ecules into inversion dimers, and weak C-H?O hydrogen bonds and ?-? inter-actions between the benzene rings of the quinazoline ring systems [centroid-centroid distance = 3.538?(3)?Å] further consolidate the packing.

| S-EPMC3379431 | biostudies-literature

4-(4,5-Dihydro-1H-benzo[g]indazol-3-yl)pyridinium chloride dihydrate.

Project description:In the cation of the title compound, C(16)H(14)N(3) (+)·Cl(-)·2H(2)O, the cyclo-hexa-1,3-diene ring displays a screw-boat conformation and the pyridine ring is slightly twisted with respect to the pyrazole ring with a dihedral angle of 4.56?(12)°. In the crystal, ions and water mol-ecules are linked into a three-dimensional network by classical N-H?O, N-H?Cl, O-H?Cl and O-H?O hydrogen bonds and by ?-? stacking inter-actions, with centroid-centroid distances of 3.7580?(14) and 3.7794?(14)?Å.

| S-EPMC3414298 | biostudies-literature

3-Hexadecyl-1,5-dimethyl-1H-1,5-benzo-diazepine-2,4(3H,5H)-dione.

Project description:In the title mol-ecule, C(27)H(44)N(2)O(2), the seven-membered ring adopts a boat-shaped conformation, with two C atoms of the fused benzene ring forming the stern and the methine C atom forming the prow. The hexa-decyl substituent occupies an equatorial position, with the aliphatic chain exhibibiting an extended zigzag conformation.

| S-EPMC3089251 | biostudies-literature

Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate.

Project description:The title compound, C(21)H(15)NO(4), was synthesized by reducing the Schiff base obtained from acenaphthenequinone and ethyl-4-aminobenzoate. The dihedral angle between the essentially planar 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline ring system [maximum deviation = 0.061?(2)?Å] and the benzene ring is 75.08?(10)°. In the crystal, mol-ecules are connected via weak inter-molecular C-H?O hydrogen bonds, forming a two-dimensional network. The ethyl group is disordered over two sets of sites with a refined occupancy ratio of 0.502?(12):0.498?(12).

| S-EPMC3050286 | biostudies-literature

Ethyl 2-(4-methyl-benzo-yl)-2,3-dihydro-1H-indene-2-carboxyl-ate.

Project description:The title compound, C20H20O3, contains two fused rings with a quaternary carbon centre connecting p-toluoyl and eth-oxy-carbonyl groups. The dihedral angle between the fused benzene ring and the three-C-atom plane (derived from O=C-C-C=O) is 82.5?(4)°, whereas the dihedral angle between the planes of the benzene rings is 53.4?(2)°. In the crystal, molecules are linked via C-H?Oester hydrogen bonds, forming chains propagating along [010].

| S-EPMC3629534 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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