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Introduction ============ Silver-catalyzed transformations of alkynes have attracted much attention over the past decade \[[@R1]--[@R2]\]. As a powerful π-activator, silver can promote various reactions of alkynes in high efficiencies \[[@R3]--[@R8]\]. Generally speaking, the proceeding of these reactions involves the activation of alkyne bond by coordination of \[Ag\] and then the attacking of nucleophilic partners, followed by a protodemetalation step to form the alkene motif ([Scheme 1](#C1){ref-type="fig"}, path a) \[[@R9]--[@R11]\]. However, the formation of a silver carbene intermediate, which could be generated usually from relevant diazo precursors \[[@R12]--[@R14]\], appears to be an unusual event in silver-mediated reactions of alkynes ([Scheme 1](#C1){ref-type="fig"}, path b). In 2007, Echavarren and co-workers have developed an intramolecular cyclopropanation reaction of 1,6-enynes by silver catalysis, involving probably the generation of a silver-carbene species \[[@R15]\]. Wang and co-workers reported a range of propargylic esters tethered to cyclohexadienones that can be converted into complex polycycles by Ag-carbenoid-initiated cascades \[[@R16]\]. Recently, Zhu's group developed a tandem 1,3‑dipolar cycloaddition/cyclopropanation silver-catalyzed reaction of enynals with alkenes \[[@R17]\]. In our previous studies, this silver carbene species could be also involved mechanistically in the Ag-mediated reaction of enynals with conjugated dienes \[[@R18]\] and the homodimerization of enynals \[[@R19]--[@R20]\]. So, the studies on the reactions of alkynes involving the generation of silver carbene species from non-diazo precursors are of great value for getting some insight into silver-carbene chemistry. ![Two modes of reactions of alkynes by silver catalysis.](Beilstein_J_Org_Chem-15-2623-g006){#C1} The generation of α-imino gold carbene intermediates in gold-catalyzed reactions of alkynes has been widely studied in recent years \[[@R21]--[@R30]\]. In 2015, Ye and co-workers, as pioneers, developed this chemistry with the employment of isoxazole nucleophiles in gold-catalyzed formal \[3 + 2\] cycloaddition reaction of ynamides \[[@R31]--[@R32]\], and zinc-catalyzed the reaction of ynol ethers \[[@R33]\], giving the respective multi-substituted pyrrole derivatives efficiently ([Scheme 2](#C2){ref-type="fig"}) \[[@R34]--[@R35]\]. The reaction proceeds via an α-imino gold carbene pathway presumed by mechanistic studies and theoretical calculations. Following our ongoing interest in the alkyne chemistry \[[@R36]--[@R38]\], we recently envisaged that the reaction of ynamides with isoxazoles could proceed under silver catalysis conditions, involving the generation of α-imino silver carbene and subsequent cyclization to pyrroles ([Scheme 2](#C2){ref-type="fig"}). Herein we want to provide some detailed results on the reaction ([Scheme 2](#C2){ref-type="fig"}), leading to the synthesis of a variety of functionalized 5-amino-1*H*-pyrrole-3-carboxamide derivatives in high yields. The reaction features the use of an inexpensive catalyst, mild reaction conditions, simple operation and product purification. Notably, the core skeleton of these products is the substructure of many biologically active molecules. For example ([Fig. 1](#F1){ref-type="fig"}), compound **1** has significant activities as DNA-cleaving agent \[[@R39]\] and sangivamycin **2** has been in clinical trials against colon cancer, gall bladder cancer and acute myelogenous leukemia in humans \[[@R40]\] and its 2-aza analogue **3** is also active against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) \[[@R41]\]. To the best of our knowledge, this case of α-imino silver-carbene is not yet reported \[[@R42]\]. ![Reactions of ynamides or ynol ethers with isoxazoles by transition metal catalysis.](Beilstein_J_Org_Chem-15-2623-g007){#C2} ![Selected bioactive molecules containing the 5-amino-1*H*-pyrrole-3-carboxamide motif.](Beilstein_J_Org_Chem-15-2623-g002){#F1}