13618-93-4Relevant articles and documents
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Arh-Lipovac,Seiwerth
, p. 992,994 (1953)
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Efficient and Direct Synthesis of γ-Amino-α,β-Unsaturated Amides by Catalyzed Allylic Substitution of α-Fluoroenamides: Toward to Synthesis of Hybrid Peptides and Indolizidines
Reddy, K. Harsha vardhan,Bédier, Matthieu,Bouzbouz, Samir
, p. 1455 - 1459 (2018)
A variety of γ-amino-α,β-unsaturated amides have been synthesized from readily available α-fluoroenamides precursors via an unprecedented intermolecular and intramolecular conjugative catalytic amination process. These γ-amino-α,β-unsaturated amides are useful intermediates for accessing rarely synthesized hybrid peptides, αγα sequences, and various classes of alkaloids containing a pyrrolidine ring, as illustrated by total synthesis of the indolizidine alkaloid coniceine.
Facile and short synthesis of (±) 1-hydroxy indolizidine and (±) coniceine from picolinic acid ethyl ester via cross claisen condensation
Veeraswamy,Anjaiah,Yennam, Satyanarayana,Jayashree
, p. 1667 - 1670 (2015)
New short synthesis of (±) 1-hydroxy indolizidine (4) and (±) coniceine (5) are described starting from picolinic acid ethyl ester (6). The key steps are the conversion of the picolinic acid ethyl ester into β-keto ester 7 via cross Claisen condensation and hydrogenation of the β-keto ester in to hydroxy bicyclic amide (8) using PtO2/H2.
Silver Ion Induced Rearrangement of N-Chloramines. Isolation of an Ionic Product in High Yield
Schell, Fred M.,Ganguly, Rathindra N.
, p. 4069 - 4070 (1980)
Treatment of N-chlorogranatanine with silver tetrafluoroborate in benzene followed by hydride reduction provides δ-coniceine in high yield. Similarly, N-chloro derivatives of nortropane and trans-decahydroquinoline provided pyrrolizidine and 1-azabicyclodecane, respectively. Under these reaction conditions, only small amounts of secondary amines are found in the product. The rearrangement product of N-chlorogranatanine was isolated without hydride reduction and shown to be the expected immonium ion product.
A CONVENIENT SYNTHESIS OF 1-AZABICYCLOALKANES AND THEIR LACTAMS VIA CUPRATES OF FORMAMIDINES
Edwards, Philip D.,Meyers, A. I.
, p. 939 - 942 (1984)
Piperidine and pyrrolidine formamidines, transformed into their α-metalloderivatives are alkylated with bifunctional electrophiles and cyclized, on formamidine removal, to the title compounds.
Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids
Quevedo-Acosta, Yovanny,Jurberg, Igor D.,Gamba-Sánchez, Diego
, p. 239 - 243 (2020/01/02)
A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.
ELECTROLYTE, ELECTROLYTIC SOLUTION, AND ELECTROCHEMICAL DEVICE USING THE SAME
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, (2010/04/30)
Disclosed herein is an electrolyte having excellent long-term reliability, a high withstanding voltage (a wide potential window), and high conductivity. The electrolyte contains a quaternary ammonium salt represented by the following general formula (1): wherein R1 represents a hydrocarbon group; R2 represents a hydrocarbon group, a hydrogen atom, or a halogen atom; R3 to R14 each represent an alkyl group, a fluoroalkyl group, a hydrogen atom or a halogen atom, C and C* each represent a carbon atom, N represents a nitrogen atom; h, i, j, x, y, and z are each an integer of 0 to 6, (h+x) is an integer of 0 to 6, (i+y) and (j+z) are each an integer of 1 to 6; and X? represents a counter anion having a HOMO energy of ?0.60 to ?0.20 a.u. as determined by the first-principle calculation on molecular orbital of the counter anion.
