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
摘要:
A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.
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
摘要:
A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.
[DE] REAKTIONSPRODUKTE VON OXAZOLIDINDERIVATEN UND BISOXAZOLIDINDERIVATEN, INSBESONDERE MIT DERIVATEN VON HYDROXYAROMATEN UND STICKSTOFFHALTIGEN VERBINDUNGEN WIE AMINOTRIAZINEN<br/>[EN] REACTION PRODUCTS OF OXAZOLIDINE DERIVATIVES AND OF BISOXAZOLIDINE DERIVATIVES, IN PARTICULAR WITH DERIVATIVES OF HYDROXYAROMATICS AND OF NITROGEN-CONTAINING COMPOUNDS, SUCH AS AMINOTRIAZINES<br/>[FR] PRODUITS DE RÉACTION DE DÉRIVÉS D'OXAZOLIDINE ET DE DÉRIVÉS DE BISOXAZOLIDINE, NOTAMMENT AVEC DES DÉRIVÉS DE COMPOSÉS HYDROXY AROMATIQUES ET DES COMPOSÉS CONTENANT DE L'AZOTE TELS QUE DES AMINOTRIAZINES
申请人:BOREALIS AGROLINZ MELAMINE GMB
公开号:WO2010018177A1
公开(公告)日:2010-02-18
Die Erfindung betrifft monomere, oligomere und polymere Reaktionsprodukte von Oxazolidinderivaten und Bisoxzolidinderivaten, insbesondere Reaktionsprodukte mit stickstoffhaltigen Verbindungen wie Aminotriazinen oder mit modifizierten Hydroxyaromaten. Eine beispielhafte Verbindung weist die folgende Struktur auf: Formel (I)