58805-10-0Relevant articles and documents
A Kulinkovich entry into tertiary N-acyliminium ion chemistry
Ollero, Lourdes,Mentink, Gertjan,Rutjes, Floris P. J. T.,Speckamp, W. Nico,Hiemstra, Henk
, p. 1331 - 1334 (1999)
(formula presented) Subjection of N-alkenylimides to Kulinkovich cyclopropanation conditions led to different types of N,O-acetals, which were used as precursors for tertiary N-acyliminium ion chemistry. In this way, a variety of bi- and tricyclic lactams were efficiently synthesized.
THE SYNTHESIS, REDUCTION AND CYCLISATION OF N-(3-BUTENYL)-MORPHOLIN- AND -THIOMORPHOLIN-2,6-DIONES
Hadley, M. S.,King, F. D.,Martin, R. T.
, p. 91 - 94 (1983)
A novel one-step synthesis of N-(3-butenyl)imides (1) from dicarboxylic acids, and sodium borohydride reduction/formic acid cyclisation of the N-(3-butenyl)-morpholin- and thiomorpholin-2,6-diones are described.
TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR
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Paragraph 0339-0340, (2019/01/04)
Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.
Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams
Ding, Guangni,Lu, Bin,Li, Yuyuan,Wan, Jun,Zhang, Zhaoguo,Xie, Xiaomin
, p. 1013 - 1021 (2015/03/30)
Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.
Stereoselective synthesis of amido and phenyl azabicyclic derivatives via a tandem aza prins-ritter/friedel-crafts type reaction of endocyclic N-acyliminium ions
Indukuri, Kiran,Unnava,Deka, Manash J.,Saikia, Anil K.
, p. 10629 - 10641 (2013/11/19)
A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one, and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one derivatives via endo-trig (aza-Prins type) cyclization followed b
Titanium- And Lewis acid-mediated cyclopropanation of imides
Bertus, Philippe,Szymoniak, Jan
, p. 659 - 662 (2008/02/05)
We report a straightforward synthesis of 1-azaspirocyclopropane lactams from imides. Following the described procedure, polycyclic nitrogen heterocycles containing a cyclopropane unit could be obtained from unsaturated imides.
β-, γ- and δ-Lactams as conformational constraints in ring-closing metathesis
Tarling, Chris A.,Holmes, Andrew B.,Markwell, Roger E.,Pearson, Neil D.
, p. 1695 - 1701 (2007/10/03)
The azabicycloalkenones 5, 6 and 7 were formed in excellent yields via ring-closing metathesis of the bis-alkenyl precursors 1, 2 and 3.
Ring-closing olefin metathesis for the synthesis of fused nitrogen heterocycles
Martin, Stephen F.,Chen, Hui-Ju,Courtney, Anne K.,Liao, Yusheng,Paetzel, Michael,Ramser, Melissa N.,Wagman, Allan S.
, p. 7251 - 7264 (2007/10/03)
A novel technique for the efficient synthesis of fused nitrogen heterocycles containing various combinations of five- and eight-membered rings has been developed. This method features the ring-closing metathesis (RCM), which is catalyzed by the molybdenum
Novel route to fused nitrogen heterocycles by olefin metathesis
Martin, Stephen F.,Liao, Yusheng,Chen, Hui-Ju,Paetzel, Michael,Ramser, Melissa N.
, p. 6005 - 6008 (2007/10/02)
A novel technique for the efficient synthesis of fused nitrogen heterocycles has been developed that features the molybdenum alkylidene-catalyzed metathesis of α,ω-dienes containing a nitrogen atom in the chain linking the two olefinic functional groups. The starting materials may be readily prepared in three steps from succinimide and glutarimide via sequential Mitsunobu alkylation, sodium borohydride reduction, and addition of a vinyl cuprate to an N-acyliminium salt generated in situ.
A practial method for N-alkylation of succinimide and glutarimide
Gesson, J. P.,Jacquesy, J. C.,Rambaud, D.
, p. 227 - 231 (2007/10/02)
Succinimide and glutarimide are N-alkylated in high yield using primary chlorides, bromides or tosylates under solid-liquid PTC conditions (K2CO3, benzene or toluene at reflux, 1percent 18-C-6).Addition of 0.1 eq of KI increases the rate of the reaction for less reactive halides such as 2-bromobutane.Keywords: imide / phase transfer catalysis / N-alkylation
