Tandem transformations of tetrahydrobenzothieno[2,3-c]pyridines in the presence of activated alkynes

First synthesis of heterocyclic allenes – benzazecine derivatives

“…synthetic methods for a series of azocines annelated with pyrrole, 12 chromene, 13 benzothiophene, 14 thiophene 15 and indole 16 were developed. It was shown that tetrahydroisoquinolines with 1-phenyl substituents reacted with methyl propiolate and acetylacetylene to give the expected benzazocines in good yields.…”

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

“…It was unusual to obtain spiro compound 3 from the interaction with DMAD. Previously, we reported that such spiro compounds form in the reaction of activated alkynes with tetrahydropyridines [ c ]-connected with a five-membered heterocycle, with one heteroatom condensed with a benzo- or hetaryl-containing fragment [18,19]. …”

Recent Advances in the Synthesis of Hydrogenated Azocine-Containing­ Molecules

“…Over the last 8 years this method was successfully applied to the synthesis of various annulated azocines: triazolopyrimido[4,5- d ]azocines 21 , 7 8 tetrahydro[1]benzothieno[3,2- d ]azocines 22 , 9 hexahydropyrimido[4,5- d ]azocines 23 and -[5,4- d ]azocines 24 , 10 tetrahydropyrimido[4,5- d ]azo­cines 25 , 11 tetrahydrobenzofuro[3,2- d ]azocine 26 , 12 tetrahydrothieno[2,3- d ]azocines 27 , 13 tetrahydroazocino[5,4- b ]indoles 28 , 14 15 hexahydropyrimidothieno[3,2- d ]azocines 29 , 16 17 and benzo[ d ]azocines 30 , 18 including systems obtained for the first time, tetrahydrothieno[3,2- d ]azocines 31 19 and tetrahydrochromeno[4,3- d ]azocine 32 (Figure 1 ). 20…”