246540-50-1Relevant academic research and scientific papers
Synthetic method of 3-aminopyrrolidine hydrochloride
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Paragraph 0085-0088, (2021/03/31)
The invention discloses a synthetic method of 3-aminopyrrolidine hydrochloride. The synthetic method comprises the steps: S1, carrying out cyclization reaction on a compound I and a compound II to obtain a compound III; S2, reacting the compound III under the action of hydrogen halide gas to obtain a compound IV; S3, reacting the compound IV with organic sulfonamide in the presence of alkali to obtain a compound V; and S4, reacting the compound V with acid to obtain a compound VI. According to the synthetic method of the 3-aminopyrrolidine hydrochloride, aryl and alkyl sulfonic groups are introduced to protect two amino groups, and during deprotection, a single reaction condition can be used, so that operation steps are effectively reduced; when benzyl is used for protecting ammonia, precious metal palladium and high-pressure catalytic hydrogenation are used for deprotection, the production cost is high, the operation risk is high, aryl and alkane sulfonic groups are used for protection, only acid is used for catalytic hydrolysis for deprotection, and the reaction condition is mild.
Chemoselective reduction of 2-acyl-N-sulfonylpyrroles: Synthesis of 3-pyrrolines and 2-alkylpyrroles
You, Hai Tao,Grosse, Andrew C.,Howard, James K.,Hyland, Christopher J. T.,Just, Jeremy,Molesworth, Peter P.,Smith, Jason A.
experimental part, p. 3948 - 3953 (2011/06/21)
The partial reduction of pyrroles is not a common practice even though it offers a potential route to pyrroline building blocks, commonly used for synthesis. We have investigated the reduction of 2-acyl-N-sulfonylpyrroles and by varying the hydride source
Direct synthesis of previously inaccessible bridgehead azabicyclics by intramolecular cyclization of α-sulfonamido and α-sulfonimido radicals
Paquette,Choon Sup Ra,Schloss,Leit,Gallucci
, p. 3564 - 3573 (2007/10/03)
Syntheses of the first bridgehead sultams and the only known bridgehead disulfonimide are described. Both approaches capitalize on the electrophilicity of α-sulfonyl radicals and their propensity to undergo intramolecular ring closure. Where double bonds are concerned, 5-exo and 6-exo pathways operate preferentially as long as structural strain is not excessive. When the reaction center is a carbon - carbon triple bond, the first cyclization gives rise to vinyl radicals that hold sufficient reactivity to capture solvent benzene. In the case of 45, this sequential reaction leads importantly to the introduction of a styrene functionality sufficiently activated to allow a second ring closure to be kinetically feasible. The solid-state structural features of 12 and 17 have been elucidated by X-ray crystallographic methods. Despite key differences from the norm in the alignment of the nitrogen lone pair relative to the adjacent sulfonyl groups, these compounds exhibit good hydrolytic stability. For 13, generation of the α-sulfonamide carbanion is possible and regiospecific oxidation with chromyl acetate has been achieved.
Synthesis and protein kinase C inhibitory activities of balanol analogs with replacement of the perhydroazepine moiety
Lai, Yen-Shi,Mendoza, José S.,Jagdmann Jr., G. Erik,Menaldino, David S.,Biggers, Christopher K.,Heerding, Julia M.,Wilson, Joseph W.,Hall, Steven E.,Jiang, Jack B.,Janzen, William P.,Ballas, Lawrence M.
, p. 226 - 235 (2007/10/03)
Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their biological activities evaluated against both PKC and cAMP-dependent kinase (PKA). The results suggested that the activity and the isozyme/kinase selectivity of these compounds are largely related to the conformation about this nonaromatic structural element of the molecules.
