共查询到20条相似文献,搜索用时 15 毫秒
1.
Mukund G. Kulkarni Yunnus B. Shaikh Ajit S. Borhade Attrimuni P. Dhondge Sanjay W. Chavhan Mayur P. Desai Deekshaputra R. Birhade Nagorao R. Dhatrak Ramesh Gannimani 《Tetrahedron: Asymmetry》2010,21(19):2394-2398
The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from d-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. 相似文献
2.
4-Acetylamino-1-phenyl-1,4-dihydro-3(2H)-isoquinolinones and 4-amino-1-phenylisoquinolin-3-ol, prepared from the corresponding 4-hydroxyimino compounds, were converted into new isoquinolines containing fused oxazole, thiazole and 1,4-oxazine rings. 相似文献
3.
Werner Lwe Sonja Witzel Norbert Matzanke Joachim Buddrus 《Journal of heterocyclic chemistry》1997,34(6):1721-1723
The Synthesis of the title compound is described and its structure elucidated by 1H nmr spectroscopy. 相似文献
4.
《Mendeleev Communications》2022,32(5):678-679
Previously unavailable 7-oxindolylidene-1,3-dimethyl-3a,9adiphenylimidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines were obtained in 63–90% yields by skeletal amidine rearrangement of the thiazolo-triazine system in the corresponding imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazines on treatment with sodium methoxide. 相似文献
5.
6.
Quaedflieg PJ Kesteleyn BR Wigerinck PB Goyvaerts NM Vijn RJ Liebregts CS Kooistra JH Cusan C 《Organic letters》2005,7(26):5917-5920
[reaction: see text] Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2. 相似文献
7.
8.
2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines
Chulakov E. N. Gruzdev D. A. Levit G. L. Sadretdinova L. Sh. Krasnov V. P. Charushin V. N. 《Russian Chemical Bulletin》2011,60(5):948-954
Kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines in the reaction with chiral 2-arylpropionyl chloride predominantly yielded R*,R*-diastereomers. Ibuprofen acyl chloride as acylating agent was found to be more selective and sensitive to the changes in
the reaction temperature as compared to naproxen acyl chloride and 2-phenylpropionyl chloride. 相似文献
9.
Hirotaka Kudo Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1984,21(6):1761-1764
The synthesis of naphtho[1′,2′:4,5]thieno[2,3-c]quinoline ( 11 ) and four monomethyl isomers is described. 相似文献
10.
Hamid Reza Shaterian Marziyeh Sedghipour Ebrahim Mollashahi 《Research on Chemical Intermediates》2014,40(8):2721-2728
We report a new, one-pot, efficient, four-component condensation of hydrazine hydrate, ethyl acetoacetate, arylaldehydes, and malononitrile in the presence of a reusable weakly basic ionic liquid, 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate, as catalyst, for synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole derivatives under solvent-free conditions at room temperature. The method has several advantages, for example good yields, short reaction times, and simple work-up procedure. 相似文献
11.
The syntheses of 5,11-dioxo-1,2,3,11a-tetrahydro-5H11H- and 5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo-[2,1-c][1,4]benzothiazepine 10 and 11 have been studied. The former was obtained by intramolecular cyclization with CDI of N-(2-mercaptobenzoyl)-L-proline 19 , prepared on one hand by demethylation of N-(2-methylthiobenzoyl)-L-proline t-butyl ester 15 , obtained via the Pummerer rearrangement of the corresponding sulphoxide 17 and successive alkaline hydrolysis, and by deprotection of the mercapto ester 18 with TFA or trimethylsilyl iodide. The ester 15 was achieved by reaction of o-(methylthio)benzoic acid 12 with L-proline t-butyl ester or by treatment of the corresponding acid chloride 13 with L-proline and successive esterification of N-(2-methylthiobenzoyl)-L-proline 16 . On the other hand the proline 19 was also obtained by reduction with sodium dithionite of (S)-bis[2-[[2-(hydroxycarbonyl)-1-pyrrolidinyl]carbonyl]phenyl] disulphide 20 , prepared by condensation of bis(2-chlorocarbonylphenyl) disulphide 14 with L-proline. The reduction of (S)-bis[2-[[2-(chloromethyl)-1-pyrrolidinyl]carbonyl]phenyl] disulphide 28 with sodium borohydride in boiling ethanol afforded directly the benzothiazepinone 11 in 85% yield. The disulphide 28 was synthesized treating the corresponding alcohol 24 or N-(2-mercaptoben-zoyl)-L-prolinol 25 with thionyl chloride. Compound 25 was obtained by demethylation of the corresponding methylthio ether 26 oxidized to sulphoxide 27 via the Pummerer rearrangement. The acid chloride 14 by condensation with (S)-2-(chloromethyl)pyrrolidine hydrochloride gave disulphide 28 as well. The acid chlorides 13 and 14 by reaction with L-prolinol provided respectively alcohols 26 and 24 . Attempts to cyclodehydrate the mercapto alcohol 25 , obtained also by reduction of disulphide 24 , failed. 相似文献
12.
S. C. Perricone Donald F. Worth Edward F. Elslager 《Journal of heterocyclic chemistry》1970,7(3):537-542
The 1,4-cycloaddition of 2,3-dihydro-5-methylfuran (II) to 1-acetyl-1,2,3,4-te trahydro-6-[(p-hydroxybenzylidene)amino]quinoline (VIII) in the presence of boron trifluoride gave two pairs of epimers, namely dl-10-acetyl-2,3,3a,4,5,7,8,9,10,11b-decahydro-4-(p-hydroxyphenyl)-11b-methylfuro[3,2-c]pyrido[2,3-g]quinoline (IXa and b) and dl-8-acetyl-2,3,3a,4,5,8,9,10,11,-11c-decahydro-4-(p-hydroxyphenyl)-11c-methylfuro[2,3-a][4,7]phenanthroline (Xa and b). dl-9-Acetyl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-hydroxyphenyl)-10b-methyl-2H-furo[3,2-c] pyrrolo-[2,3-g]quinoline (XIIIa) was the predominant product isolated from the reaction of II with 1-acetyl-5-[p-(hydroxybenzylidene)amino]indoline (XII). When 1-acetyl-6-[(p-hydroxybenzylidene)amino]indoline (XVI) was treated with 2,3-dihydro-5-methylfuran (II), two epimers of dl-7-acetyl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-hydroxyphenyl)-10b-methyl-2H-furo[3,2-c]pyrrolo[3,2-g]quinoline (XVIIa and b) were obtained. dl-2,3,3a,4,5,6b,8,9,9a,10,11,12b-Dodecahydro-4,10-bis(p-methoxyphenyl)-6b,12b-dimethylfuro[3,2-c]furo[2′,3′:4,5]pyrido[2,3-g]quinoline (XX) was formed when 2,3-dihydro-5-methylfuran was allowed to react with N,N'-bis(p-methoxybenzylidene)-p-phenylcnediamine (XIX). Structure assignments were made from NMR spectra. None of the compounds exhibited appreciable biological activity. 相似文献
13.
14.
Edward F. Elslager Donald F. Worth S. C. Perricone 《Journal of heterocyclic chemistry》1969,6(4):491-495
Catalytic reductive scission of 4-methylcinnoline (V) with Raney nickel afforded o-amino-β-methylphenethylamine (IV) in 57% yield. Treatment of IV with carbon disulfide followed by thermal cyclization of the product furnished 1,3,4,5-tetrahydro-5-methyl-2H-1,3-benzodiazepine-2-thione (III). Reaction of III with ethyl chloroacetate, ethyl 2-bromohexanoate, ethyl 2-chloroacetoacetate, 2-bromo-2′-methoxyacetophenone, and 2-bromoacetophenone provided a series of substituted 5,6-dihydro-6-methylthiazolo[2,3-b][1,3]benzodiazepines. Condensation of III with 2-chlorocyclopentanone and 2-chlorocyclohexanone gave 2,3,10,11-tetrahydro-10-methyl-1H-cyclopenta[4,5]thiazolo[2,3-b][1,3]benzodiazepine and 7,8,9,10,12,13-hexahydro-13-methylbenzothiazolo[2,3-b][1,3]benzodiazepine, respectively. Structure assignments are discussed. None of the compounds possessed appreciable biological activity. 相似文献
15.
Canoy WL Cooley BE Corona JA Lovelace TC Millar A Weber AM Xie S Zhang Y 《Organic letters》2008,10(6):1103-1106
A one-step diastereoselective (up to 98:2) synthesis of the bis-furan alcohol of Darunavir and other HIV drug candidates has been achieved utilizing the novel cyclization of glycolaldehyde and 2,3-dihydrofuran. The cycloaddition was catalyzed by a variety of catalysts including those formed from tin(II) triflate and common chiral ligands such as BINAP and Evans's box ligands. An efficient and unique enzymatic process enhanced the enantiomeric purity to provide the target in optically pure form. 相似文献
16.
3:4-Fused furocoumarins and pyrrolocoumarins are synthesised from 3-hydroxy and 3-benzamido-substituted coumarins by a novel two step sequence. 相似文献
17.
18.
Eresko A. B. Raksha E. V. Berestneva Yu. V. Muratov A. V. Voitash A. A. Tolkunov V. S. Tolkunov S. V. 《Russian Journal of Organic Chemistry》2020,56(11):1929-1936
Russian Journal of Organic Chemistry - A new synthetic approach to fused azepines was demonstrated on an example of the synthesis of 2-methyl-2,3,4,5-tetrahydro-1H-[1]benzothieno[2,3-c]azepine. The... 相似文献
19.
Phaedon M. Hadjimihalakis 《Journal of heterocyclic chemistry》1991,28(4):1111-1114
A novel annelated benzofuroxan 4 and a benzofurazan 4a have been prepared in good yields. Nitration of 5 afforded both trinitro derivatives 6 and 7 . Low temperature nmr spectroscopy was applied on compound 4 and the value ΔG* is reported. 相似文献
20.
Marjo Merslavi
Andrej Petri
Branko Stanovnik Miha Tiler 《Journal of heterocyclic chemistry》1989,26(3):581-583
The transformations of 7-methyl-7H- and 8-methyl-8H-pyrazolo[4, 3-d]tetrazolo[1, 5-b]pyridazines 1, 2, 9 and 10 into 8-methyl-8H- and 9-methyl-9H-pyrazolo[3, 4-H]-s-triazolo[4, 3-b]pyridazines 7 and 8 , and 1-methyl-1H-and 2-methyl-2H-imidazo[1, 2-b]pyrazolo[3, 4-d]pyridazines 13 and 14 are described. 相似文献