22217-77-2Relevant articles and documents
Reactions of cyclopropyl aryl ketones with sulfonamides mediated by Zr(OTf)4: Cascade preparation of 5-aryl-3,4-dihydro-2H-pyrrole
Shi, Min,Yang, Yong-Hua,Xu, Bo
, p. 1622 - 1624 (2004)
We found that the Lewis acid Zr(OTf)4 can effectively promote the ring-opening reaction of cyclopropyl aryl ketones with sulfonamides. By controlling the reaction conditions, we could obtain the ring-opened products 3 and the cyclized products 5 in moderate to good yields. This process provides a novel and efficient route for the synthesis of 5-aryl-3,4-dihydro-2H-pyrrole in the presence of a Lewis acid.
Synthesis of 2-aryl-1-pyrrolines from arylnitriles
Keppens, Marian,De Kimpe, Norbert,Fonck, Gwendolien
, p. 3097 - 3102 (1996)
Aromatic nitriles underwent addition of stabase-protected γ-aminopropylmagnesium bromide to afford the corresponding 1-pyrrolines in one step. Copyright
Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf
Zhuang, Daijiao,Gatera, Tharcisse,An, Zhenyu,Yan, Rulong
, p. 771 - 775 (2022/01/20)
The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes
Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions
Ban, Kazuho,Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari,Tomita, Naohito
, p. 3481 - 3484 (2021/06/17)
We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).
Intramolecular Csp3-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines
Jiao, Ning,Li, Xinyao,Luo, Xiao,Song, Song,Wang, Weijin,Wen, Xiaojin
, p. 4482 - 4487 (2020/05/18)
The intramolecular Csp3-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp3-H and/or C-C bond cleavage. Two C-N single bonds or a CN double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.
Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
Wang, Yiqiong,Huang, Fei,Zhang, Songlin
, p. 5178 - 5181 (2020/08/13)
The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
Huang, Fei,Zhang, Songlin
, p. 7430 - 7434 (2019/10/11)
A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol
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Paragraph 0026; 0027; 0028; 0029; 0086-0089, (2019/05/22)
The invention discloses a method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol. In the atmosphere of inert gas, the amino alcohol and the enol serve as raw materials, potassium tert-butoxide is used as alkali, a series
Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles
Legarda, Pablo D.,García-Rubia, Alfonso,Arrayás, Ramón Gómez,Carretero, Juan C.
, p. 3947 - 3954 (2018/06/11)
The dual role of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the presence of N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is both highly efficient and tolerant to a variety of steric and electronic changes at both coupling partners. By adequate choice of reductive conditions, the N-sulfonyl deprotection can be directed to the selective formation of benzo-fused pyrrolizidine or fused pyrrolidino-benzazapine frameworks.
The reaction of cyclic imines with the Ruppert-Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine
Shevchenko, Nikolay E.,Vlasov, Katja,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
scheme or table, p. 69 - 74 (2011/02/27)
We have demonstrated that the Ruppert-Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding α-trifluoromethyl derivatives of nitrogen heterocycles. 5-7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized.
