14 research outputs found
1H and 13C NMR assignments for a series of Diels–Alder adducts of anthracene and 9‐substituted anthracenes
Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/111949/1/mrc4268.pd
4-(8-Ethoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4-yl)butane-1-peroxol
In the title molecule, C18H23NO3, the hydroperoxybutyl substituent is nearly fully extended, with the four torsion angles in the range 170.23 (10)–178.71 (9)°. The O—O distance in the hydroperoxide group is 1.4690 (13) Å. This group acts as an intermolecular hydrogen-bond donor to a quinoline N atom. This results in dimeric units about the respective inversion centers, with graph-set notation R
2
2(18)
Antibacterial flavonoids from the fruits of Macaranga hurifolia
Pagna JIM, Awazi T, Mbarga PE, et al. Antibacterial flavonoids from the fruits of Macaranga hurifolia. Journal of Asian Natural Products Research . 2022.As part of our search for new secondary metabolites from Macaranga hurifolia Beille, a phytochemical investigation was carried out on the fruits that led to the isolation and characterization of two new prenylated flavonol derivatives named macafolias A (1) and B (2), along with five known compounds. Their chemical structures were established on the basis of extensive analysis of their 1-D and 2-D NMR (1H, 13C, APT, COSY, HSQC and HMBC) in conjunction with mass spectroscopy and by comparison with data from the literature. The invitro assay of the antibacterial potency of the crude extract, fractions and some pure compounds were evaluated against a wide range of bacteria strains
Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and 2,3,4,5-Tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines from Skraup–Doebner–Von Miller Quinoline Synthesis and Their Implications for the Mechanism of That Reaction
The real mechanism of the Skraup–Doebner–Von
Miller
quinoline synthesis remains controversial and not well understood
despite several mechanistic studies reported on the matter. A series
of unexpected and unusual 5,6,7,8,9,10-hexahydro-6,6-pentamethylenephenanthridines
and 2,3,4,5-tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines have been obtained through the Skraup–Doebner–Von
Miller quinoline synthesis. On the basis of these unexpected results
and in agreement with some of the previously reported quinoline syntheses,
an alternative mechanistic pathway is proposed for this variant of
the reaction. It involves the formation of a Schiff base through a
reaction between the ketone and the aniline derivative in the first
step, followed by a cycloalkenylation at the <i>ortho</i>-position to the amine functional group of the aniline derivative,
and an annulation in the final step to close the quinoline ring, leading
to a dihydroquinoline derivative. To the best of our knowledge, this
is the first report of such a mechanistic pathway being proposed for
any variant of the Skraup–Doebner–Von Miller quinoline
synthesis
Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and 2,3,4,5-Tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines from Skraup–Doebner–Von Miller Quinoline Synthesis and Their Implications for the Mechanism of That Reaction
The real mechanism of the Skraup–Doebner–Von
Miller
quinoline synthesis remains controversial and not well understood
despite several mechanistic studies reported on the matter. A series
of unexpected and unusual 5,6,7,8,9,10-hexahydro-6,6-pentamethylenephenanthridines
and 2,3,4,5-tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines have been obtained through the Skraup–Doebner–Von
Miller quinoline synthesis. On the basis of these unexpected results
and in agreement with some of the previously reported quinoline syntheses,
an alternative mechanistic pathway is proposed for this variant of
the reaction. It involves the formation of a Schiff base through a
reaction between the ketone and the aniline derivative in the first
step, followed by a cycloalkenylation at the <i>ortho</i>-position to the amine functional group of the aniline derivative,
and an annulation in the final step to close the quinoline ring, leading
to a dihydroquinoline derivative. To the best of our knowledge, this
is the first report of such a mechanistic pathway being proposed for
any variant of the Skraup–Doebner–Von Miller quinoline
synthesis
Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and 2,3,4,5-Tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines from Skraup–Doebner–Von Miller Quinoline Synthesis and Their Implications for the Mechanism of That Reaction
The real mechanism of the Skraup–Doebner–Von
Miller
quinoline synthesis remains controversial and not well understood
despite several mechanistic studies reported on the matter. A series
of unexpected and unusual 5,6,7,8,9,10-hexahydro-6,6-pentamethylenephenanthridines
and 2,3,4,5-tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines have been obtained through the Skraup–Doebner–Von
Miller quinoline synthesis. On the basis of these unexpected results
and in agreement with some of the previously reported quinoline syntheses,
an alternative mechanistic pathway is proposed for this variant of
the reaction. It involves the formation of a Schiff base through a
reaction between the ketone and the aniline derivative in the first
step, followed by a cycloalkenylation at the <i>ortho</i>-position to the amine functional group of the aniline derivative,
and an annulation in the final step to close the quinoline ring, leading
to a dihydroquinoline derivative. To the best of our knowledge, this
is the first report of such a mechanistic pathway being proposed for
any variant of the Skraup–Doebner–Von Miller quinoline
synthesis