Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride

2015 ◽  
Vol 70 (4) ◽  
pp. 221-223 ◽  
Author(s):  
Jin Wang ◽  
Teng-huo-sheng Liao ◽  
Jian Yang

AbstractThe title compound (5) was prepared by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via the Blanc reaction, oxidation and alkylation. The described method provides a good yield of the C-6 heterocyclic-substituted benzoquinone derivative and is suitable for the synthesis of other benzoquinone derivatives.

1995 ◽  
Vol 60 (4) ◽  
pp. 715-718 ◽  
Author(s):  
Vladimír Pouzar ◽  
Ivan Černý

The title compound X was prepared according to the recently published procedure for preparation of analogous derivatives in the 5β-pregnane series, using the reaction sequence I -> II -> III -> IV -> V -> VI -> VII -> VII -> IX -> X (total yield 18%). The configuration at ring D centers (14β,17α) follows from the structure of the starting ketone I and was also checked by comparing diol IV with the sample prepared by an independent route. The epimeric purity at C-17 was carefully monitored during the whole synthesis by 1H NMR spectra (singlet of 18-H3).


2014 ◽  
Vol 662 ◽  
pp. 59-62
Author(s):  
Shan Shan Gong ◽  
Qi Sun

A facile and efficient method for the synthesis ofP1,P3-dizidovudine-5′,5′-triphosphate has been developed. The coupling of zidovudine diphosphate with zidovudine phosphoropiperidate based on the DCI activation of P-N bond afforded the desired product in good yield.


1994 ◽  
Vol 49 (9) ◽  
pp. 1207-1214 ◽  
Author(s):  
Helmut Fischer ◽  
David Reindl ◽  
Gerhard Roth

An efficient synthesis of diarylallenylidene pentacarbonyl chromium and tungsten com­plexes is presented. Irradiation of M(CO)6 in THF affords (CO)sM[THF], Substitution of the THF ligand by diarylpropargylalcoholate and subsequent desoxygenation with COCF gives the title compounds in good yield. (The structure of diphenylallenylidene pentacarbonyl chromium has been determined by X-ray structure analysis


1987 ◽  
Vol 65 (1) ◽  
pp. 189-190 ◽  
Author(s):  
Michel Girard ◽  
David B. Moir ◽  
John W. ApSimon

The title compound 1 was prepared in 13% overall yield starting from the commercially available and inexpensive 3,5-dimethoxybenzoic acid (4). The n-pentyl side chain was elaborated from cross-coupling reactions between halides.


2009 ◽  
Vol 2009 (4) ◽  
pp. 205-207 ◽  
Author(s):  
Samir Ghosh ◽  
A. Sanjeev Kumar ◽  
G.N. Mehta ◽  
R. Soundararajan ◽  
Subhabrata Sen

An efficient synthesis of 4-oxazolinephenylboronic acid from 4-bromobenzoic acid is reported. The title compound couples with heteroaryl halides in presence of Pd(PPh3)4 and Na2CO3 in aqueous toluene to give heterobiaryl oxazolines.


Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 951-954
Author(s):  
Kosho Makino ◽  
Yumi Hasegawa ◽  
Takahide Inoue ◽  
Koji Araki ◽  
Hidetsugu Tabata ◽  
...  

A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.


2002 ◽  
Vol 2002 (1) ◽  
pp. 11-12 ◽  
Author(s):  
Abd El-Wareth Sarhan ◽  
Taeko Izumi

2-(3-Methylbutoxy)-1,3-benzodithiole has been synthesised in good yield by a modification of the method previously described by Nakayama.


1977 ◽  
Vol 30 (12) ◽  
pp. 2689 ◽  
Author(s):  
JM McLaren ◽  
RV Stick ◽  
S Webb

The conversion of 2-acetamido-2-deoxy-D-glucose into 2-acetamido-3,4,6- tri-O-acetyl-2-deoxy-α-D-glucosyl chloride has been reinvestigated and the chloride transformed, with some modification of the literature method, into 2,2,2-trichloroethyl 2-acetamido-4,6-O-benzylidene-2- deoxy-β-D-glucoside. This compound has been converted into the title compound by the sequence acetylation, acid hydrolysis and selective acetylation. An efficient synthesis of benzyl 2,3-di-O-acetyl-β-D- galacto-pyranosideis reported and its unsuccessful selective acetylation contrasted with the above.


1990 ◽  
Vol 68 (1) ◽  
pp. 69-73 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Mahmood Tajerbashi ◽  
Steven J. Rettig ◽  
James Trotter

Reaction of oxybis(diphenylborane) with the condensation product of salicylohydroxamic acid and cyclopentanone gives the title compound in good yield. Crystals of 2,2-diphenyl-4,4-tetramethylene-1,3,5-trioxa-3a-azonia-2-borata-2,3,4,5-tetrahydro-1H-cyclopenta[a]naphthalene are monoclinic, a = 12.521(1), b = 12.409(1), c = 12.975(1) Å, β = 93.784(8)°, Z = 4, space group P21/n. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.043 and Rw = 0.044 for 1502 reflections with I ≥ 2σ(I). The molecule has a typical diphenylboron hydroxamate structure featuring a five-membered COBON chelate ring. The O,O-chelating ligand is weakly bound to the diphenylboron moiety. Bond lengths (corrected for libration) include: (N)O—B = 1.558(4), (C=)O—B = 1.578(4), and C—B = 1.589(5) and 1.603(5) Å. Keywords: crystal structure, boron compound, organoboron compound.


Sign in / Sign up

Export Citation Format

Share Document