Regioselective synthesis of 5-alkylidene and 5-(iodoalkylidene)-pyrrol-2(5H)-ones by halolactamisation of (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides

The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

“…Abarbri and coworkers6 have recently indicated that a minimal number of synthetic methods exist for the construction of the ylidenepyrrol-2(5H)-ones (1) although more extensive strategies exist for the corresponding ylidenefuran-2(5H)-ones. The same workers6 have utilized a very efficient methodology (Scheme 1) involving (Z)-3-iodoalk-2-enamides (7) for the preparation of the 5-(iodoalkylidene)-pyrrol-2(5H)-ones (9).…”

“…The same workers6 have utilized a very efficient methodology (Scheme 1) involving (Z)-3-iodoalk-2-enamides (7) for the preparation of the 5-(iodoalkylidene)-pyrrol-2(5H)-ones (9). The Sonogashira coupling of the (Z)-3-iodoalk-2-enamides (7) produced good yields of the (Z)-alk-2-en-4-ynamides (8), which underwent cyclization with ICl to give an E/Z mixture of the 5-(iodoalkylidene)-pyrrol-2(5H)-ones (9) with the E isomer normally predominating.…”

Regioselective Synthesis of 1,4,6-Trisubstituted-2-Pyridinones and 2,3-Disubstituted (2H)-Isoquinolin-1-ones via Tandem Stille Reaction/Heterocyclisation

“…16 We have also reported the synthesis of dienamides and enynamides from dienoic acids 17 or by iodovinylic amides and alkyne reagents. 18 These methodologies were then applied to the synthesis of g-tributyltin methylidenebutenolides 19 and g-alkylidene pyrrol-2(5H)-ones. 18 In continuation of our studies on the synthesis of unsaturated heterocycles, 20 we have recently described our first results on the synthesis of the 2-pyridinones by approaches involving intramolecular addition of amides to allenylstannanes (Scheme 1).…”

“…18 These methodologies were then applied to the synthesis of g-tributyltin methylidenebutenolides 19 and g-alkylidene pyrrol-2(5H)-ones. 18 In continuation of our studies on the synthesis of unsaturated heterocycles, 20 we have recently described our first results on the synthesis of the 2-pyridinones by approaches involving intramolecular addition of amides to allenylstannanes (Scheme 1). 21 We now present our full results in this field and their extension to regioselective synthesis of isoquinolinones.…”

Synthesis of Heterocycles and Carbocycles by Electrophilic Cyclization of Alkynes

“…6-Aryl-11H-indolo[3,2-c]quinolines are prepared by the Pd-catalyzed carbonylative cyclization of o-(ol-aminophenylethynyl)trifluoroacetanilide and aryl halides (Equation 2.95) [136].Bicyclic lactams have also been prepared by the Pd-catalyzed cross-coupling of simple acetylene-containing lactams and aryl or vinylic halides (Equation 2.96)[137] 72. 2 Synthesis of Heterocycles and Carbocycles by Electrophilic Cyclization of Alkynes Finally, simple alkenynamides react readily with ICl to afford stereoisomeric mixtures of the corresponding five-membered ring iodolactams (Equation 2.97)[138].…”