-
Je něco špatně v tomto záznamu ?
Polymer-Assisted Synthesis of Single and Fused Diketomorpholines
P. Králová, S. Benická, M. Soural,
Jazyk angličtina Země Spojené státy americké
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- acylace MeSH
- alkylace MeSH
- cyklizace MeSH
- kyselina trifluoroctová chemie MeSH
- kyseliny karboxylové chemie MeSH
- molekulární struktura MeSH
- morfoliny chemická syntéza MeSH
- nitrobenzeny chemie MeSH
- oxaziny chemie MeSH
- polymery chemie MeSH
- silany chemie MeSH
- stereoizomerie MeSH
- techniky syntézy na pevné fázi metody MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The synthesis of different diketomorpholines via N-acyl-3,4-dihydro-2 H-1,4-oxazine-3-carboxylic acids is reported in this article. The key intermediates were prepared using a convenient solid-phase synthesis starting from polymer-supported Ser( tBu)-OH. After subsequent sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), alkylation with an α-bromoketone, cleavage of the 4-Nos group and acylation with an α-halocarboxylic acids, acid-mediated cleavage from the resin yielded dihydrooxazine-3-carboxylic acids in high crude purities. Depending on the reaction conditions, exposure to base resulted in cyclization to either oxazino[3,4- c][1,4]oxazine-diones or 3-methylidenemorpholine-2,5-diones. Further reaction with triethylsilane-trifluoroacetic acid (TES/TFA) led to olefin reduction, in the case of oxazino[3,4- c][1,4]oxazine-dione with full control of the newly formed stereocenter.
Citace poskytuje Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc20006649
- 003
- CZ-PrNML
- 005
- 20200528095902.0
- 007
- ta
- 008
- 200511s2019 xxu f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1021/acscombsci.8b00176 $2 doi
- 035 __
- $a (PubMed)30640439
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a xxu
- 100 1_
- $a Králová, Petra $u Department of Organic Chemistry, Faculty of Science , Palacký University , 771 46 Olomouc , Czech Republic.
- 245 10
- $a Polymer-Assisted Synthesis of Single and Fused Diketomorpholines / $c P. Králová, S. Benická, M. Soural,
- 520 9_
- $a The synthesis of different diketomorpholines via N-acyl-3,4-dihydro-2 H-1,4-oxazine-3-carboxylic acids is reported in this article. The key intermediates were prepared using a convenient solid-phase synthesis starting from polymer-supported Ser( tBu)-OH. After subsequent sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), alkylation with an α-bromoketone, cleavage of the 4-Nos group and acylation with an α-halocarboxylic acids, acid-mediated cleavage from the resin yielded dihydrooxazine-3-carboxylic acids in high crude purities. Depending on the reaction conditions, exposure to base resulted in cyclization to either oxazino[3,4- c][1,4]oxazine-diones or 3-methylidenemorpholine-2,5-diones. Further reaction with triethylsilane-trifluoroacetic acid (TES/TFA) led to olefin reduction, in the case of oxazino[3,4- c][1,4]oxazine-dione with full control of the newly formed stereocenter.
- 650 _2
- $a acylace $7 D000215
- 650 _2
- $a alkylace $7 D000478
- 650 _2
- $a kyseliny karboxylové $x chemie $7 D002264
- 650 _2
- $a cyklizace $7 D003500
- 650 _2
- $a molekulární struktura $7 D015394
- 650 _2
- $a morfoliny $x chemická syntéza $7 D009025
- 650 _2
- $a nitrobenzeny $x chemie $7 D009578
- 650 _2
- $a oxaziny $x chemie $7 D010078
- 650 _2
- $a polymery $x chemie $7 D011108
- 650 _2
- $a silany $x chemie $7 D012821
- 650 _2
- $a techniky syntézy na pevné fázi $x metody $7 D060327
- 650 _2
- $a stereoizomerie $7 D013237
- 650 _2
- $a kyselina trifluoroctová $x chemie $7 D014269
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1_
- $a Benická, Sandra $u Department of Organic Chemistry, Faculty of Science , Palacký University , 771 46 Olomouc , Czech Republic.
- 700 1_
- $a Soural, Miroslav $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry , Palacký University , Hněvotínská 5 , 779 00 , Olomouc , Czech Republic.
- 773 0_
- $w MED00179493 $t ACS combinatorial science $x 2156-8944 $g Roč. 21, č. 3 (2019), s. 154-157
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/30640439 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y a $z 0
- 990 __
- $a 20200511 $b ABA008
- 991 __
- $a 20200528095900 $b ABA008
- 999 __
- $a ok $b bmc $g 1525507 $s 1096705
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2019 $b 21 $c 3 $d 154-157 $e 20190118 $i 2156-8944 $m ACS combinatorial science $n ACS comb. sci. $x MED00179493
- LZP __
- $a Pubmed-20200511
