13618-93-4Relevant articles and documents
HYDROBORATION-CARBONYLATION OF BISOLEFINIC AMINES: A FACILE SYNTHESIS OF δ-CONICEINE
Garst, Michael E.,Bonfiglio, John N.
, p. 2075 - 2076 (1981)
Treatment of N-allyl-N-3-butenyl-N-Cbz-amine (1) with thexyl borane followed by cyanidation affords an azacyclononanone 2 in 35 percent yield which can be transformed into δ-coniceine (3) by catalytic reduction.
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.
2-Aza-2,4-cyclopentadione. Existence and Reactivity
Gavina, F.,Costero, A. M.,Andreu, M.R.,Carda, M.,Luis, S.V.
, p. 4017 - 4018 (1988)
The elusive species 2-aza-2,4-cyclopentadienone has been generated from an insoluble polymeric precursor.The liberated intermediate can act either as diene or as a dienophile in Diels-Alder reactions.
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
supporting information, 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.
A concise and diastereoselective synthesis of piperidine and indolizidine alkaloids via aza-Prins cyclization
Reddy, Basi V. Subba,Chaya, Dudhmal N.,Yadav, Jhillu S.,Gree, Rene
experimental part, p. 297 - 303 (2012/03/26)
The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2- hydroxy-methyl piperidine have been accomplished in a highly diastereo-selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids. Georg Thieme Verlag Stuttgart · New York.
ELECTROLYTE, ELECTROLYTIC SOLUTION, AND ELECTROCHEMICAL DEVICE USING THE SAME
-
, (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.
Novel synthesis of indolizidines and quinolizidines
Tehrani, Kourosch Abbaspour,D'hooghe, Matthias,De Kimpe, Norbert
, p. 3099 - 3108 (2007/10/03)
A very short synthesis of indolizidines, quinolizidines and some higher homologues was developed by alkylation of 2-methyl-1-pyrroline or 6-methyl-2,3,4,5-tetrahydropyridine with 1,3- or 1,4-dihaloalkanes, followed by reduction of the intermediate iminium salts, resulting in the desired 1-azabicyclo[m.n.0]alkanes in good yields.
