10530-89-9Relevant articles and documents
General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations
Zubkov, Fedor I.,Nikitina, Eugenia V.,Galeev, Timur R.,Zaytsev, Vladimir P.,Khrustalev, Victor N.,Novikov, Roman A.,Orlova, Daria N.,Varlamov, Alexey V.
, p. 1659 - 1690 (2014/02/14)
An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.
Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: Convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives
Banfi, Luca,Basso, Andrea,Guanti, Giuseppe,Kielland, Nicola,Repetto, Claudio,Riva, Renata
, p. 2151 - 2160 (2007/10/03)
A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular SN2 reaction was studied. 1 -Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were ob