Synthesis Of Tricyclic Derivatives Research Articles

ChemInform Abstract: Inter‐ and Intramolecular Dienamine Organocatalytic Strategies for the Synthesis of Tetrahydroisoquinolines and Tricyclic Derivatives via [3 + 2] and [4 + 2] Cycloadditions

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Inter- and Intramolecular Dienamine Organocatalytic Strategies for the Synthesis of Tetrahydroisoquinolines and Tricyclic Derivatives via [3+2] and [4+2] Cycloadditions

The use of dienamines represents a new approach for carrying out asymmetric aminocatalytic reactions controlled by a remote chiral catalyst. In this account, we describe our contributions on the use of dienamine methodologies for the synthesis of interesting compounds from a natural product and pharmaceutical point-of-view. Dienamine aminocatalysis is employed for the synthesis of tetrahydroisoquinoline derivatives via intermolecular [3+2] cycloadditions, and for the preparation of tricyclic products by means of intramolecular [4+2] Diels–Alder reactions. 1 Introduction 2 Intermolecular Dienamine versus Iminium Ion Catalysis: Synthesis of Tetrahydroisoquinoline Derivatives 3 Intramolecular Dienamine Catalysis: Synthesis of Tricyclic Derivatives 4 Outlook

Ring-opening metathesis and ring-closing metathesis of bicyclo[4.2.0]octene-ynes: Application to the synthesis of tricyclic compounds

Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of bicyclo[4.2.0]octene-ynes and their application to the synthesis of tricyclic derivatives have been demonstrated using a second-generation ruthenium carbene complex. When bicycloalkene having a propargylamino group as an alkyne tether was reacted with a second-generation ruthenium carbene complex under an ethylene atmosphere, ROM-RCM proceeded to give tricyclic heterocycles in good yield. On the other hand, when the effect of the substituent on the alkyne was examined, cross metathesis (CM) of the alkyne part with ethylene proceeded to provide a conjugated diene derivative.

ChemInform Abstract: Design and Synthesis of Tricyclic Derivatives as High Density Lipoprotein Cholesterol Enhancers.

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Design and synthesis of tricyclic derivatives as high density lipoprotein cholesterol enhancers

A pharmacophore for increasing HDLC was proposed based on common structural features of non-thio-containing compounds with HDLC enhancing properties. A search of the compound database identified various series of these non-thio-containing compounds, including a novel tricyclic imidazoisoquinolone. Preparation of l-aryl-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamides using a novel and widely applicable one-step process from 2-acyl benzoic acids is reported. Reaction of diamines with 1-aryl-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamides and related aza-analogues proceeded with regio-control to furnish imidazoisoquinolones, pyrimidoisoquinolones, and imidazonaphthyridines. NMR studies and X-ray crystallography confirmed the regiochemistry of the products. Compounds of these series increased concentrations of HDLC in test animals following oral administration.

Stereoselective synthesis of tricyclic derivatives of 2-amino-1-pyrrolin-5-one dimethyl acetals

Reactions of a tetracyanobicycloalkene (1) with methanol and ethylene glycol give derivatives of 2-aminopyrrolin-5-one (2 and 3), and acid hydrolysis of3 gives an imide (4). According to an X-ray structural investigation, acis orientation of the heterocycle (with respect to the C=C bond) is realized in2; in the case of4, thecis/trans ratio of the isomers in the crystal and solution is 2∶1.

Synthesis of tricyclic compounds with sulfur and silicon heteroatoms in the central ring

The synthesis of tricyclic derivatives which contain both silicon and sulfur in a central six-, seven- and eight-membered ring are described. Phenothiasilin-5,5-dioxides are prepared by treatment of ( o-LiC 6H 4) 2SO 2 with dichlorosilanes. Reduction of the sulfone group is described as well as attempts to introduce aminopropyl substituents at silicon. Thiasilepins are prepared from the Grignard reagent of ( o-BrC 6H 4CH 2SC 6H 4Br- o) and reactions of this ring system are described. Reaction of Me 2Si(C 6H 4CH 2Br- o) with Na 2S gave a thiasilocin derivative.

Silicon analogs of phenothiazine

Synthesis of tricyclic derivatives which contain both silicon and nitrogen in the central ring (phenazasilines) as well as a dimethylaminopropyl side chain bonded either to Si or to N are described. Reaction of 4,4′-dibromo-2,2′-dilithio- N-(γ-dimethylaminopropyl)diphenylamine with Me 2SiCl 2 provides a ring brominated silicon analog of the tranquilizer promazine. Reaction of 4,4′-dibromo-2,2′-dilithio- N-methyldiphenylamine with MeSiHCl 2 followed by SiH addition of the phenazasiline to allylamine provided the isomeric derivative. Debromination of three phenazasilines with BuLi followed by hydrolysis demonstrated formation of both 2-bromophenazasilines as well as phenazasilines. Structural comparisons to phenothiazines are discussed.