Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones

Abstract

A novel and efficient one-pot synthesis of 3,4-dihydronaphthalen-1(2H)-ones by employing 2-iodocyclohex-2-enones, 1-alkynes, and a Pd[(C 6 H 5 ) 3 P] 4 /AgOAc catalytic system is described. The attractive features of this method, which enables the facile preparation of 3,4-dihydronaphthalen-1(2H)-one derivatives, are its very simple and straightforward procedure, mild reaction conditions, and good yields (65-87%).

Semisynthesis and Biological Evaluation of Platensimycin Analogues with Varying Aminobenzoic Acids

“…Four additional aminobenzoate analogues of PTM 8–10 were smoothly synthesized from PTM in a one‐step reaction (Scheme ). Electrophilic iodination of PTM (I 2 , DMAP, pyridine, CCl 4 ) afforded the 5′‐I‐platensimycin 8 in a good yield of 88% . Treatment of PTM by 65% HNO 3 in 5 min furnished the 5′‐nitro substituted PTM analogue 9 in 84% yield.…”

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

“…Triyne 1a was obtained from 2-cyclohexenone using a six-step synthesis with 35% overall yield (Scheme ). 2-Iodocyclohex-2-enone 4 was obtained from 2-cyclohexenone using a described procedure . It then underwent a Sonogashira reaction to yield enyne 5 .…”

“…2-Iodocyclohex-2enone 4 was obtained from 2-cyclohexenone using a described procedure. 29 enyne 5. The ketone was reduced using dibutylaluminum hydride to yield enynol 6.…”