2740-00-3Relevant academic research and scientific papers
Formation of lactams via photoelectron-transfer catalyzed reactions of N-allylamines with α,β-unsaturated esters
Das, Suresh,Dileep Kumar,Shivaramayya, Kalchar,George, Manapurathu V.
, p. 3425 - 3434 (1996)
Anthraquinone photosensitized reactions of a few N-allylamines with α,β-unsaturated esters have been investigated. These reactions led predominantly to the formation of lactams along with trace amounts of products arising out of tandem radical addition reactions. A mechanism is proposed involving the rearrangement of the α-aminoallyl radical, initially generated via anthraquinone photosensitized reactions, to α-aminoalkyl radicals. Subsequent reactions of these radicals with α,β-unsaturated esters can lead to the observed products.
Radical carboazidation of alkenes: An efficient tool for the preparation of pyrrolidinone derivatives
Renaud, Philippe,Ollivier, Cyril,Panchaud, Philippe
, p. 3460 - 3462 (2002)
A one-pot intermolecular radical carboazidation of alkenes is reported. The utility of the reaction is demonstrated by the development of a three-component preparation of pyrrolidinones, pyrrolizidinones [Eq. (a)], and indolizidinones starting from benzen
Radical Carboazidation: Expedient Assembly of the Core Structure of Various Alkaloid Families
Panchaud, Philippe,Ollivier, Cyril,Renaud, Philippe,Zigmantas, Sarunas
, p. 2755 - 2759 (2004)
A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated
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.
Rapid Synthesis of Bicyclic N-Heterocyclic Cores from N-Terminal α,β-Unsaturated Diazoketones
Santiago, Jo?o Victor,Burtoloso, Antonio C. B.
, p. 2822 - 2830 (2018/06/04)
A method for the synthesis of bicyclic N-heterocyclic cores from N-terminal α,β-unsaturated diazoketones has been developed. The transformation involves three sequential steps that include N-deprotection, an intramolecular aza-Michael, and a photochemical Wolff rearrangement as a one-pot protocol. By using this strategy, a series of substituted bicyclic N-heterocycles, particularly, indolizidines and pyrrolizidines, were synthesize in good yields.
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
supporting information, p. 1455 - 1459 (2018/04/06)
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.
Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)-H Alkenylation and Application to Alkaloid Synthesis
Holstein, Philipp M.,Dailler, David,Vantourout, Julien,Shaya, Janah,Millet, Anthony,Baudoin, Olivier
, p. 2805 - 2809 (2016/02/27)
A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp3)-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for acce
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 (2015/03/04)
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.
Efficient and regioselective 9-endo cyclization of α-carbamoyl radicals
Song, Liyan,Liu, Kun,Li, Chaozhong
supporting information; experimental part, p. 3434 - 3437 (2011/08/21)
With the promotion of Lewis acid BF3?OEt2, various N-(hex-5-enyl)-2-iodoalkanamides underwent efficient and regioselective 9-endo iodine-atom-transfer radical cyclization reactions at room temperature. The cyclized products were readily converted to the corresponding azonan-2-ones by reduction with Bu3SnH or to hexahydroindolizin-3(5H)-ones by treatment with aqueous Na2CO3 in a one-pot, two-stage manner.
Evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase
Shankaran,Donnelly, Karla L.,Shah, Shrenik K.,Guthikonda, Ravindra N.,MacCoss, Malcolm,Humes, John L.,Pacholok, Stephen G.,Grant, Stephan K.,Kelly,Wong
, p. 4539 - 4544 (2007/10/03)
Syntheses and evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2- imines as inhibitors of nitric oxide synthase (NOS) are discussed. An extensive SAR was established for pyrrolidin-2-imines class of compounds. The amidines came out as the most potent inhibitors in addition to displaying selectivity.
