. Author manuscript; available in PMC: 2021 May 3.

Published in final edited form as: European J Org Chem. 2020 Feb 13;2020(16):2379–2383. doi: 10.1002/ejoc.201901855

Table 1.

Reactions of triyne 8 with several C,N-diaryl imines.


entry	imine	product [step i^a: yield%, step ii^b: yield%]
1	2a, X = H, Y = H	*12a* [step i^a: 98%, step ii^b: 68%]
2	2b, X = NO₂, Y = H	*12b* [step i^a: 68%, step ii^b: 90%]
3	2c, X = OMe, Y = H	*12c* [step i^a: 78%, step ii^b: 86%]
4	2d, X = H, Y = NO₂	*12d* [step i^a: 62%, step ii^b: 82%]
5	2e, X = H, Y = OMe	*12e* [step i^a: 100%, step ii^b: 97%]
6	2f, X = NO₂, Y = NO₂	*12f* [step i^a: 19%, step ii^b: 56%]
7	2g, X = OMe, Y = OMe	*12g* [step i^a: 88%, step ii^b: 89%]

yield of the 1,4-dihydroacridine from the HDDA reaction

yield of the acridine adduct following MnO₂ treatment