- Palladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigations
-
With Pd(OAc)2/pyridine as the catalyst system and molecular oxygen as a green oxidant, acrylanilides and N-allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylani
- Yip, Kai-Tai,Yang, Dan
-
supporting information; experimental part
p. 2166 - 2175
(2011/10/12)
-
- Sequential combination of ruthenium-, base-, and gold-catalysis - A new approach to the synthesis of medicinally important heterocycles
-
A general approach to the high-yielding synthesis of medicinally important heterocycles was achieved through the sequential combination of ring-closing metathesis, base-induced ring opening (BIRO), hydroamination, and a Diels-Alder reaction of functionalized allyl-(2-allylphenyl)amines in the presence of a catalytic amount of Grubbs' second-generation catalyst, base (tBuOK), and [AuCl(PPh3)]/AgOTf. Herein, we also demonstrate the important electronic factors in the BIRO of N-substituted-benzo[b]azepines for the regioselective synthesis of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl) phenylamines in very good yields with high purity; these are very good, useful compounds in medicinal chemistry. We also discovered the selective cascade synthesis of privileged hexahydrophenanthridines from (Z)-N-substituted-2-(buta- 1,3-dienyl)phenylamines by gold catalysis in moderate to good yields with >99 % diastereomeric excess. The possible reaction mechanism for the unusual hydroamination followed by [4+2] cycloaddition of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl)phenylamines through gold catalysis is discussed in this work. A novel process for the synthesis of highly substituted, medicinally important heterocycles was achieved through the sequential combination of ring-closing methathesis, base-induced ring opening, hydroamination, and Diels-Alder reaction of functionalized allyl-(2-allylphenyl) amines in the presence of a catalytic amount of [Ru], base, and [Au] (see scheme). Copyright
- Ramachary, Dhevalapally B.,Narayana, Vidadala V.
-
p. 3514 - 3522
(2011/08/06)
-
- Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reaction
-
Chemical equation presented A new method for the synthesis of tricyclic nitrogen heterocycles from N/,2-diallylaniline derivatives Is described. These transformations proceed via sequential alkene amlnopalladation of an Intermediate LnPd(Ar)(NRR') species followed by alkene carbopalladatlon of the resulting LnPd(Ar)(R) complex. Both alkene insertion steps occur in preference to C-N or C-C bond-forming reductive elimination. An unusual 1,3palladium shift occurs when 2-Allyl-N-(2-vinylphenyl) aniline Is employed as substrate, which yields a tetracyclic molecule with three contiguous stereocenters.
- Schultz, Danielle M.,Wolfe, John P.
-
supporting information; experimental part
p. 1028 - 1031
(2010/06/15)
-
- Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines
-
Two new series of 1,4-epoxy-2-exo-vinyl(isopropenyl)tetrahydro-1- benzazepines and cis-2-vinyl(isopropenyl)-4-hydroxytetrahydro-1-benzazepines were prepared by an efficient three/four-step route from available substituted N,N-diallylanilines and mono N-al
- Acosta, Lina María,Palma, Alirio,Bahsas, Alí
-
experimental part
p. 8392 - 8401
(2010/11/19)
-
- Sequential aza-Claisen rearrangement and ring-closing metathesis as a route to 1-benzazepine derivatives
-
A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance. Georg Thieme Verlag
- Ghosh, Debalina,Thander, Latibuddin,Ghosh, Sanjay K.,Chattopadhyay, Shital K.
-
experimental part
p. 3011 - 3015
(2009/06/27)
-