- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
-
We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
-
supporting information
p. 9419 - 9424
(2021/11/30)
-
- Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
-
The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.
- Kim, Hyejin,Kim, Taehoon,Lee, Dong Gil,Roh, Sang Weon,Lee, Chulbom
-
supporting information
p. 9273 - 9276
(2014/08/05)
-
- Synthesis of some biologically active 2,6-dichloro-1-(N-substituted phenyl)-1,4-dihydropyridine-3,5-Dicarbaldehydes using vilsmeier-haack reaction and their applications
-
Various 2,6-dichloro-1-(N-substituted phenyl)-1,4-dihydropyridine-3,5- dicarbaldehydes were synthesized in two steps using moderate conditions and 3,5-diformyl groups were transformed into different functionalities. The synthesized compounds were screened
- Rajput,Girase
-
p. 201 - 208
(2013/09/24)
-
- Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation
-
A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
- Kim, Hyun Jin,Kim, Jiyu,Cho, Seung Hwan,Chang, Sukbok
-
supporting information; experimental part
p. 16382 - 16385
(2011/12/13)
-
- Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine
-
This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst. Copyright
- Ito, Masato,Sakaguchi, Ayaka,Kobayashi, Chika,Ikariya, Takao
-
p. 290 - 291
(2008/04/18)
-
- Concise and short synthesis of functionalized 5,6-dihydropyridin-2-ones by means of palladium(0)-catalyzed cross-coupling of ketene aminal phosphates
-
A concise and short synthetic entry to 5,6-dihydropyridin-2-one derivatives has been developed by means of palladium(0)-catalyzed cross-coupling of cyclic ketene aminal phosphates.
- Fuwa, Haruhiko,Kaneko, Akane,Sugimoto, Yasuaki,Tomita, Taisuke,Iwatsubo, Takeshi,Sasaki, Makoto
-
p. 101 - 106
(2007/10/03)
-
- Antinociceptive properties of N-aryl-glutaramic acids and N-aryl-glutarimides
-
This study describes the antinociceptive activity of some N-aryl-glutaramic acids and N-aryl-glutarimides in writhing and formalin tests, two classical models of pain in mice. These compounds show high activity, being more active than acetyl salycilic aci
- Stiz,Souza,Golin,Neto,Correa,Nunes,Yunes,Cechinel-Filho
-
p. 942 - 944
(2007/10/03)
-
- N-CYANOIMIDES: REACTIVITY WITH AMINE NUCLEOPHILES
-
N-Cyanoimides are useful precursors to N-alkyl or N-aryl imides.Treatment of aromatic N-cyanoimides such as N-cyanophthalimide (1) with primary amines provides N-substituted imides directly, while aliphatic N-cyanoimides afford diamide intermediates which can be converted to N-substituted imides upon heating.
- Stephens, Randall W.,Domeier, Linda A.,Todd, Michael G.,Nelson, Veronica A.
-
p. 733 - 736
(2007/10/02)
-
- REACTIVITY OF IMINOPHOSPHORANES TOWARDS SOME SYMMETRICAL DICARBONYL DICHLORIDES : SYNTHESES AND MECHANISMS
-
In situ generated iminophosphoranes 1 react with dicarbonyl dihalides 2a-b and 3a-c to give known or new nitrogen heterocycles.The proposed mechanisms involve elimination of either triphenyl-phosphine oxide or dichlorotriphenylphosphorane depending upon both the iminophosphorane and the dicarbonyl compound.
- Aubert, Thierry,Farnier, Michel,Guilard, Roger
-
-
- SYNTHESIS AND REACTIONS OF N-(p-CHLOROSULPHONYLPHENYL)-SUCCINIMIDE, -GLUTARIMIDE AND -CAMPHORIMIDE
-
N-Phenyl-succinimide, -glutarimide and -camphorimide mreact with chlorosulphonic acid to yield the corresponding sulphonyl chlorides.Condensation with nucleophiles afforded 25 sulphonyl derivatives, which are to be examined for biocidal properties. reacti
- Cremlyn, Richard,Nunes, Ricardo
-
p. 183 - 186
(2007/10/02)
-
- Free Radical Reactions of N-Heterocyclic Compounds, VI. - Radical Reactions of Cyclic 2,2-Diacyl-1-arylhydrazyls. - A New N-N Bond Cleavage Reaction
-
Diacylhydrazyl radicals 5 are generated from N-(phenylamino)dicarboximides 1, 2a, b, 3a-f, and 4 by oxidation with different oxidants.The intermediates 5 react in two ways depending on the substituents in the anilino group.Dimerization of the hydrazyl radikals 5 to stable tetrazanes 8 is favoured by acceptor substituents in the Ar group.N-N bond dissoziation (α-decomposition) of the hydrazyl radicals 5 is favoured by donor substituents in the phenyl ring of the anilino group.The fragments of such reactions are imide radicals 22 and phenylnitrenes 23.The formation of these fragmentation products is proven by analysis of the reaction products.The formation of benzoxazole (25) (15percent yield) is an evidence for an intramolecular insertion reaction of the o-methoxyphenylnitrene, generated by oxidation of 3e.The hydrazyl radicals 5 are also trapped by the stable free radical 2,4,6-tri-tert-butylphenoxyl (9).The thermal decomposition of the isolated radical adducts was studied.
- Schulz, Manfred,Kluge, Ralph,Willscher, Sabine
-
p. 671 - 678
(2007/10/02)
-
- A SYNTHESIS OF SUCCINIMIDES AND GLUTARIMIDES FROM CYCLIC ANHYDRIDES
-
The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermadiate monoamide to an N-hydroxysuccinimidyl ester using N,N'-disuccinimidyl oxalate
- Kometani, Tadashi,Fitz, Tony,Watt, David S.
-
p. 919 - 922
(2007/10/02)
-