Interrupted CuAAC-thiolation for the construction of 1,2,3-triazole-fused eight-membered heterocycles from O-/N-propargyl derived benzyl thiosulfonates with organic azides
| Title | Interrupted CuAAC-thiolation for the construction of 1,2,3-triazole-fused eight-membered heterocycles from O-/N-propargyl derived benzyl thiosulfonates with organic azides |
| Publication Type | Journal Article |
| Year of Publication | 2022 |
| Authors | Reddy, RJannapu, Waheed, M, Kumari, AHaritha, Krishna, GRama |
| Journal | Advanced Synthesis & Catalysis |
| Volume | 364 |
| Issue | 2 |
| Pagination | 319-325 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 1615-4150 |
| Keywords | Eight-Membered Heterocycles, Fused-Triazoles, Interrupted-Click Reaction, Thiolation, thiosulfonates |
| Abstract | A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51-94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61-74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. |
| DOI | 10.1002/adsc.202101256 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 5.837 |
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Central NMR Facility