Copper-Catalyzed Domino Addition–Cyclization Reaction between Terminal Alkynes, Carbon Disulfide, and Oxiranes

Abstract

Copper or silver salts promote a domino addition-cyclization reaction between terminal alkynes, carbon disulfide, and oxiranes in a regioselective manner to afford 1,4-oxathiane derivatives in good yield.

Copper Catalyzed Synthesis of Thiomorpholine Derivatives: A New Entry of Multicomponent Reaction Between Terminal Alkynes, Isothiocyanates, and Aziridines

“…In spite of their importance in preparation of heterocyclic compounds, the number of available reports for the reaction of metals acetylide with heterocumulene remains scarce. Ghazanfarpour reported an interesting multicomponent reaction using terminal alkynes, carbon disulfide, and oxiranes . Our group has also described a three‐component reaction involving terminal alkynes, isothiocyanates, and oxiranes catalytic in silver salts .…”

A Catalytic Route to Pyrrole Derivatives via Copper‐catalyzed Multicomponent Reaction

“…These catalytic transformations lead to the construction of complex molecules from readily available starting materials . Recently, the synthesis of various molecular frameworks through addition reactions involving metal‐acetyilides and electrophiles such as C═O, C═N, C═S, and C═C have been well developed . Carreira reported the first copper‐alkynyls additions to Michael acceptors at room temperature .…”

A simple route to morpholine derivatives via copper‐acetylide addition to carbodiimide in the presence of oxiranes

“…[17] Ghazanfarpour-Darjani reported a novel addition of metal acetylides to carbon disulfide at ambient conditions using oxirane as third coupling partner. [18] Patil and Raut developed a cooperative catalytic system for synthesis of quinolones based on nucleophilic additions of copper acetylide to 2-aminobenzaldehyde. [19] In spite of copper acetylide importance in preparation of various organic skeletons, the number of reports for the reaction of metals acetylide with carbodiimides remains scarce most likely due to the its lower reactivity compared with aldehydes and imines.…”

“…Among the solvents examined in the reaction, NMP afforded a better yield (entry 1 vs entries [10][11][12][13][14][15]. Clearly, the choice of base had a great effect on the outcome of the reaction (entries [16][17][18][19]. Both key steps (Scheme 1, formation of propargylic amidine 6 and ring-opened intermediate 7) in the reaction sequence (Scheme 1) should benefit from a more electrophilic counterion associated with tert-butoxide ion; however, Li 2 CO 3 was not a good choice for this reaction, most likely due to the low solubility in such organic media.…”