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A diastereoselective synthesis of 1-methyl-2-alkyl- and 2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic esters has been developed from methyl (2-nitrophenyl)acetate (1). The method involves alkylation of 1 with an allylic halide, ozonolysis of the double bond, and catalytic hydrogenation. The final hydrogenation initiates a tandem sequence involving (1) reduction of the aromatic nitro group, (2) condensation of the aniline or hydroxylamine(8) nitrogen with the side chain carbonyl, (3) reduction of the resulting nitrogen intermediate, and (4) reductive amination of the tetrahydroquinoline with formaldehyde produced in the ozonolysis to give a methyl (+/-)-1-methyl-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylate. Removal of the formaldehyde prior to hydrogenation gives the simple (+/-)-2-alkyl derivatives. The products are isolated in high yield as single diastereomers having the C-2 alkyl group cis to the C-4 carboxylic ester. The reaction has been extended to the synthesis of tricyclic structures with similar high diastereoselection. 相似文献
2.
Richard A. Bunce Sharadsrikar V. Kotturi Christopher J. Peeples Elizabeth M. Holt 《Journal of heterocyclic chemistry》2002,39(5):1049-1054
A tandem SN2‐Michael addition reaction has been developed for the synthesis of cis‐ and trans‐fused nitrogen and sulfur heterocycles from the cis and trans isomers of ethyl (±)‐(2E)‐3‐[2‐(iodomethyl)cyclo‐hexyl]‐2‐propenoate. Octahydro‐1H‐isoindole‐1‐acetic acid and octahydrobenzo[c]thiophene‐1‐acetic acid derivatives have been prepared and their stereochemistries elucidated using NMR and X‐ray crystallo‐graphic methods. Cyclization substrates for both the cis‐ and the trans‐fused rings are readily available in four steps from known compounds. Yields for the cyclization range from 80‐85% and stereochemical selec‐tivities with respect to the side chain vary from 12.5‐16:1 for the cis‐fused structures to 6‐7.5:1 for the trans‐fused structures. Steric interactions in the transition states for ring closure are proposed to rationalize the observed preferences. 相似文献
3.
Santosh R. Kotturi Brinda Somanadhan Jun-Hong Ch’ng Kevin S.-W. Tan Mark S. Butler Martin J. Lear 《Tetrahedron letters》2014
We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue. 相似文献
4.
Richard A. Bunce Derrick M. Herron Jason R. Lewis Sharadsrikar V. Kotturi Elizabeth M. Holt 《Journal of heterocyclic chemistry》2003,40(1):101-106
A two‐step diastereoselective synthesis of linear‐fused tricyclic nitrogen heterocycles has been developed from cyclic β‐ketoesters. The cyclization substrates are readily prepared by alkylation of the methyl 2‐oxo‐cycloalkanecarboxylates with 2‐nitrobenzyl bromide. Hydrogenation of these substrates initiates a reaction sequence involving (1) reduction of the aromatic nitro group, (2) condensation of the resulting hydroxyl‐amine or aniline nitrogen with the cycloalkanone and (3) reduction of the imine. The products are isolated in high yield as single diastereomers having the trans‐fused ring junction. The observed selectivity is rationalized in terms of a steric effect imposed by the ester group in the final reductive amination step which directs the incoming hydrogen to the opposite face of the molecule. By comparison, reductive cyclizations of substrates lacking the stereodirecting ester group give mixtures of cis and trans products with a preference for the cis‐fused heterocycle. 相似文献
5.
Santosh R. Kotturi 《Tetrahedron letters》2009,50(37):5267-375
With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP). 相似文献
6.
Richard A. Bunce Derrick M. Herron Jason R. Lewis Sharadsrikar V. Kotturi 《Journal of heterocyclic chemistry》2003,40(1):113-120
N‐Phenyl‐substituted pyrrolidines and piperidines have been synthesized by catalytic reduction of nitrobenzene in the presence of 4‐ and 5‐oxoaldehydes, respectively. The process involves reduction of the aromatic nitro group to give the N‐phenylhydroxylamine or aniline followed by reductive amination with the two carbonyl functional groups. Monocyclic systems are generally formed in high yield and are easily purified. The method has also been extended to the synthesis of fused N‐phenylazabicyclics from 2‐(3‐oxo‐propyl)cycloalkanones. A high degree of diastereoselectivity for the trans‐fused product is observed in substrates having an ester group α to the cycloalkanone carbonyl. Bicyclic precursors lacking this ester group give mixtures of cis and trans products. Finally, contrary to previous reports, we have demonstrated that aniline can be substituted for nitrobenzene in these reactions. 相似文献
7.
Alfred L. Williams Srinivasa R. Dandepally Sharadsrikar V. Kotturi 《Molecular diversity》2010,14(4):697-707
The synthesis of 17 phenoxy substituted 4-chloro-N-(aryl/alkyl)thiophene-2-sulfonamides using a PMB protection/deprotection strategy is described. Nucleophilic displacement
of p-methoxybenzyl (PMB) protected 4,5-dichloro-N-(aryl/alkyl)-thiophene-2-sulfonamides was carried out with different phenols under mild basic conditions. Reaction times
of 3–6 h and overall yields of 78–98% were achieved with the PMB group in place compared to no reaction without this protecting
group. The PMB group was easily and selectively removed in 68–98% yield using TFA in DCM. 相似文献
8.
G Fuchs K-H Müller J Freudenberger K Nenkov S-L Drechsler SV Shulga D Lipp A Gladun T Cichorek P Gegenwart 《Pramana》2002,58(5-6):791-797
The effect of substitutional disorder on the superconducting properties of YNi2B2C was studied by partially replacing yttrium and nickel by Lu and Pt, respectively. For the two series of (Y, Lu)Ni2B2C and Y(Ni, Pt)2B2C compounds, the upper critical field H
c2(T) and the specific heat c
p(T, H) in the superconducting mixed state have been investigated. Disorder is found to reduce several relevant quantities such
as T
c, the upper critical field H
c2(0) at T=0 and a characteristic positive curvature of H
c2(T) observed for these compounds near T
c. The H
c2(T) data point to the clean limit for (Y, Lu) substitutions and to a transition to the quasi-dirty limit for (Ni, Pt) substitutions.
The electronic specific heat contribution γ(H) exhibits significant deviations from the usual linear γ(H) law. These deviations reduce with growing substitutional disorder but remain even in the quasidirty limit which is reached
in the Y(Ni1−x
, Pt
x
)2B2C samples for x=0.1. 相似文献
9.
Tanay Ghoshal Vishal Nagar Adilakshmi Vutla Sharadsrikar Kotturi Sasikumar Kuttappan 《Tetrahedron letters》2019,60(4):358-361
An efficient single step process for the construction of pharmaceutically relevant substituted aminobenzoxazoles have been described in this report. Various electrodes and electrolytes combinations have been carried out to harvest optimum coupling results. The presented CN bond formation reaction methodology has applied for the synthesis of biologically active compounds. This methodology saves reaction steps over traditional functionalization reactions. 相似文献
10.
Non-resonant microwave absorption (NRMA) studies of superconducting MgB2 and a sample containing ∼10% by weight of MgO in MgB2 are reported. The NRMA results indicate near absence of intergranular weak links in the pure MgB2 sample. A linear temperature dependence of the lower critical field H
c1 is observed indicating a non-s wave superconductivity. However, the phase reversal of the NRMA signal which could suggest d wave symmetry is also not observed. In the MgB2 + MgO sample, much larger low field dependent absorption is observed indicating the presence of intergranular weak links.
The hysteretic behavior of NRMA is compared and contrasted in the two samples. In the pure MgB2 sample, a large hysteresis is observed between the forward and the reverse scans of the magnetic field indicating strong
pinning of flux lines. This hysteresis saturates a few degrees below T
c while in the MgB2 + MgO sample, a much slower increase of hysteresis with decreasing temperature is observed, a signature of weaker pinning. 相似文献
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