Indexed keywords
1 ,2 ,3-TRIAZOLES;
AZIDE-ALKYNE CYCLOADDITION;
BIS-HETEROANNULATIONS;
INTRAMOLECULAR REACTIONS;
NITROGEN HETEROCYCLES;
ACETYLENE;
AROMATIC COMPOUNDS;
COPPER;
SUBSTRATES;
CATALYSIS;
1 (2,4 DIMETHOXYPYRIMIDIN 5 YL) 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1 (2,4 DIMETHOXYPYRIMIDIN 5 YL) 6,7 DIHYDRO 5H BENZO[C][1,2,3]TRIAZOLO[1,5 A]AZEPINE;
1 (4 CARBOMETHOXYPHENYL) 5,6,7,8 TETRAHYDROBENZO[C][1,2,3]TRIAZOLO[1,5 A]AZOCINE;
1 (4 METHOXYPHENYL) 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1 (4 METHOXYPHENYL) 5,6,7,8 TETRAHYDROBENZO[C][1,2,3]TRIAZOLO[1,5 A]AZOCINE;
1 (4 METHOXYPHENYL) 6,7 DIHYDRO 5H BENZO[C] [1,2,3]TRIAZOLO[1,5 A]AZEPINE;
1 (4 NITROPHENYL) 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1 (4 NITROPHENYL) 6,7 DIHYDRO 5H BENZO[C][1,2,3]TRIAZOLO[1,5 A]AZEPINE;
1 (PHENYL) 6,7 DIHYDRO 5H BENZO[C][1,2,3]TRIAZOLO[1,5 A]AZEPINE;
1 [[5 (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL) 2,2 DIMETHYLTETRAHYDROFURO[3,2 D][1,3]DIOXOL 6 YL OXY]METHYL] 6,7 DIHYDRO 5H BENZO[C][1,2,3]TRIAZOLO[1,5 A]AZEPINE;
1 [[5 (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL) 2,2 DIMETHYLTETRAHYDROFURO[3,2 D][1,3]DIOXOL 6 YLOXY]METHYL] 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1 PHENYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1 VINYL 5,6 DIHYDRO[1,2,3]TRIAZOLO[5,1 A]ISOQUINOLINE;
1,2,3 TRIAZOLE DERIVATIVE;
3 (4 METHOXYPHENYL) 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE;
3 BUTYL 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE;
3 PHENYL 8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOLE;
BENZAZEPINE DERIVATIVE;
BENZAZOCINE DERIVATIVE;
CHEMICAL COMPOUND;
COPPER;
METHYL 4 (8H [1,2,3]TRIAZOLO[5,1 A]ISOINDOL 3 YL)BENZOATE;
PALLADIUM;
PHENYL 5,6,7,8 TETRAHYDROBENZO[C][1,2,3]TRIAZOLO[1,5 A]AZOCINE;
TETRAHYDROISOQUINOLINE;
UNCLASSIFIED DRUG;
ARTICLE;
CARBON NUCLEAR MAGNETIC RESONANCE;
COLUMN CHROMATOGRAPHY;
CONFORMATIONAL TRANSITION;
CYCLIZATION;
HEATING;
MELTING POINT;
ONE POT SYNTHESIS;
PROTON NUCLEAR MAGNETIC RESONANCE;
1
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Based on control experiments and known features of palladium chemistry, a plausible reaction mechanism can be envisaged. Mechanistically, the active catalytic species Pd(0) is generated in situ by dimerization, to a small extent, of acetylenic compound 8. Next, coupling of 8 with iodide 7 takes place through the Sonogashira pathway, see: Sonogashira, K.; Tohda, Y.; Haghihara, N. Tetrahedron Lett. 1975, 50, 4467; leading to the formation of intermediate σ-alkynyl azide derivative, which is then converted into products 1-4 through intramolecular [3+2] cycloaddition between azide and alkyne moieties. An alternative mechanism involving copper-assisted regioselective [3+2] cycloaddition between acetylene and azide groups of substrates 8 and 7, leading to the formation of intermediate 1,4-substituted 1,2,3-triazoles 9 (X = I), which may undergo intramolecular coupling with aryl iodide through C-H bond activation to form the products 1-4, was ruled out on the basis of control experiments.
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