36520-39-5Relevant articles and documents
Amine protection/α-activation with the tert -butoxythiocarbonyl group: Application to azetidine lithiation-electrophilic substitution
Hodgson, David M.,Mortimer, Claire L.,McKenna, Jeffrey M.
supporting information, p. 330 - 333 (2015/01/30)
tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N′,N′-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding N-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol.
Straightforward access to cyclic amines by dinitriles reduction
Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Favre-Reguillon, Alain,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
supporting information, p. 975 - 983 (2014/01/23)
1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.
Heterocyclic derivatives and their use as antithrombotic agents
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, (2008/06/13)
The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is O or S; X′ being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents.
Synthesis of azetidine, pyrrolidines and piperidine by intramolecular cyclization of ω-Azidoboranes.
Jego, J. M.,Carboni, B.,Vaultier, M.
, p. 554 - 565 (2007/10/02)
This paper describes the development of efficient routes to azetidine, pyrrolidines and piperidines by creation of a carbon-nitrogen bond.Two complementary syntheses of these heterocycles were studied : the cyclization of ω-azidoboronic esters by treatment with boron trichloride, and the one pot hydroboration of an ω-azidoalkene and intramolecular reductive alkylation.The scope and limitations of these two promising approaches are reported.Keywords: azides / boronic esters / boranes / intermolecular cyclization / azetidine / pyrrolidine / piperidine / pyrrolizidine
Process for synthesis of azetidine and novel intermediates therefor
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, (2008/06/13)
A novel process is described for preparing azetidine and 2 or 3 methyl and ethyl azetidine free bases by reacting primary arylmethylamine having suitable bulk providing substituents attached to the methyl carbon and an appropriate propane derivative havin
SYNTHESIS OF AZETIDINE FROM 1-SUBSTITUTED AZETIDIN-3-OLS
Nitta, Yoshihiro,Kanamori, Yasuyuki
, p. 2467 - 2470 (2007/10/02)
From readily available 1-substituted azetidin-3-ols, azetidine was prepared in high yield by removal of the hydroxyl group and N-substituents.
