14376-92-2Relevant academic research and scientific papers
Aminoenylesters. I. A new synthesis of 1,2,3,4-tetrahydropyrimidines by heterocyclic annelation reactions of aminoenylesters with primary amines and acetaldehyde
Koike, Takeshi,Tanabe, Mituharu,Takeuchi, Naoki,Tobinaga, Seisho
, p. 1117 - 1119 (1997)
The reactions of aminoenylesters 3, which were prepared by the reactions of methyl propiolate (1) and primary amines 2, with primary amines 2 and acetaldehyde afforded 1,2,3,4-tetrahydropyrimidines 4. This provides a new heterocyclic annelation reaction.
A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives promoted by Ca(OTf)2
Yaragorla, Srinivasarao,Saini, Pyare Lal,Pareek, Abhishek,Almansour, Abdulrahman I.,Arumugam, Natarajan
supporting information, p. 2034 - 2038 (2016/04/26)
A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives has been reported using alkaline earth catalyst [Ca(OTf)2]. Initially aryl amine reacts with ethyl propiolate to form β-enamino ester which further reacts w
Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: A convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones
Yin, Guangwei,Zhu, Yuanxun,Wang, Ningning,Lu, Ping,Wang, Yanguang
, p. 8353 - 8359 (2013/09/02)
1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6
Synthesis of functionalized 2-aminohydropyridines and 2-pyridinones via domino reactions of arylamines, methyl propiolate, aromatic aldehydes, and substituted acetonitriles
Sun, Jing,Sun, Yan,Xia, Er-Yan,Yan, Chao-Guo
experimental part, p. 436 - 441 (2011/10/08)
An efficient and practical synthetic method for the functionalized 2-amino hydropyridines and 2-pyridinones was successfully developed via the domino reactions of arylamines, methyl propiolate, aromatic aldehydes and the substituted acetonitriles with tri
A short synthesis of (±)-cytisine
Botuha, Candice,Galley, Carl M. S.,Gallagher, Timothy
, p. 1825 - 1826 (2007/10/03)
The synthesis of racemic cytisine 1 has been completed using (i) N-selective alkylation of 6-bromopyridone with bromide 6 and (ii) Pd(o) mediated intramolecular a-arylation of lactam 8 as key steps to achieve rapid assembly of the tricyclic core skeleton of the lupin alkaloids.
Construction of Hydroxylated Alkaloids (+/-)-Mannonolactam, (+/-)-Deoxymannojirimycin, and (+/-)-Prosopinine through Aza-Annulation
Cook, Gregory R.,Beholz, Lars G.,Stille, John R.
, p. 3575 - 3584 (2007/10/02)
The aza-annulation of β-enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of δ-lactams.This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH2, followed by aza-annulation with acryloyl chloride or acrylic anhydride.Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity.The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation.The resultant δ-lactam product was used as a valuable intermediate in the synthesis of three natural products.Subsequent modification of this δ-lactam gave the naturally occurring α-mannosidase inhibitors (+/-)-mannonolactam and (+/-)-deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.
