3355-28-0Relevant articles and documents
Stereocontrolled Construction of Condensed γ-Lactam Ring Systems by Cationic Cyclizations. Rearrangement of a γ-Lactam to a δ-Lactam
Marson, Charles M.,Grabowska, Urszula,Walsgrove, Timothy,Eggleston, Drake S.,Baures, Paul W.
, p. 284 - 290 (1994)
A new condensation of 3-alkenamides with benzaldehyde in acidic media, notably polyphosphoric acid, lead to γ-lactam rings with high regio- and stereocontrol.One such γ-lactam was shown to undergo a novel and stereocontrolled ring-expansion to a δ-lactam.
Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements
Dimirjian, Christine A.,Casti?eira Reis, Marta,Balmond, Edward I.,Turman, Nolan C.,Rodriguez, Elys P.,Di Maso, Michael J.,Fettinger, James C.,Tantillo, Dean J.,Shaw, Jared T.
supporting information, p. 7209 - 7212 (2019/10/02)
The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.
Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis
Cera, Gianpiero,Lanzi, Matteo,Balestri, Davide,Della Ca, Nicola,Maggi, Raimondo,Bigi, Franca,Malacria, Max,Maestri, Giovanni
supporting information, p. 3220 - 3224 (2018/06/11)
The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.