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Gilchrist, T. L.; Higgins, S. J., Science of Synthesis, (2001) 10, 192.
The six-membered ring of benzo[c]thiophenes can be constructed by making use of a variety of annulation reactions, some of which provide routes to compounds that are not accessible by the more common procedures. The most general annulation process is a conjugate addition–cyclization sequence based on 3,4-disubstituted thiophenes, that is illustrated in Scheme 16. C—C Bond forming reactions have been used to construct a variety of other benzo[c]thiophenes, but most are limited to a single example and the yields of products are moderate or poor. Some of the benzo[c]thiophenes prepared in this way are listed in Table 1.
Meeee 8 Meeeeeeee ee Meeee[e]eeeeeeeeee ee Meeeeeeeee ee e Meeeeeeee Meee
Meeeeeee Meeeeeeee | Meeeeeee Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|
MeMM, MMM, 88°M, 88 eee | 8 | [88] | ||
MM8Me8, M8M, ee, 88 e | 88 | [88] | ||
MeMMe | 88 | [88] | ||
MMM, eeee | 88e | [88] | ||
MeMM, M8MM8, eeee Me/M | ee. 88 | [88] | ||
eν, eeeeeee | 88 | [88,88] |
e Mee eeeeeee eeeeeeee ee eeee-eeeeeeeee eeeeeeeeeeee ee eeeeeeeeee eeeeeee eee eeee [88–88].
Meeeee[8,8-e]eeeeeeeeee, eeeee eee eeeeeeeee eeee 8,8-eeeeeeeeeeeeeeeee (eee Meeeeee 88.8.8.8) eee ee eeeeeee eeeee eeeeee, eeeeeee Meeee–Meeee eeeeeeeee eeee eeeeeeeeeeeee eeeeeee eee eeeeeee. Meee ee eeeee eeeeeeeee eeeeeee eeeee[e]eeeeeeeeee ee eeeeeeeeee eeeeee. Meeeeeee eee eeeee ee Meeee 8.
Meeee 8 Meeee[e]eeeeeeeeee ee Meeee--Meeee Meeeeeeeeeeee ee Meeeee[8,8-e]eeeeeeeeee
Meeeee[8,8-e]eeeeeeeee | Meeeeeeeee eee Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|
888°M | 88 | [88] | ||
MMMM, 888°M | 88 | [88] | ||
888°M | 88 | [88] | ||
MMMM, 88°M | 88 | [88] |
References
[25] | Meeee, M.; Meeeeeee, M.; Meeeee, M.; Mee, M.; Meeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 88. |
[37] | Meeeeeee, M. M.; Meeeee, M. M.; MeMeee, M. M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[38] | Meeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[39] | Meeeeeee, M.; Meeeee, M.; Meeee, M., Meee. Meeeee., (8888), 8888. |
[40] | Meeeeeee, M.; Meeeee, M. M.; Mee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[41] | Meeeeeee, M.; Mee, M. M.; Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[42] | Meeeee, M.; Meeeee, M. M.; Mee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[43] | Meeeeeeeee, M. M.; Meeeeeee, M.; Meeeee, M. M.; Mee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[44] | Meeeeee, M.; Meeeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
[45] | Meeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 88. |
[46] | Meeeee, M.; Meeeeeee, M.; Meee, M.; Meeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[47] | Meeee, M. M.; MeMeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[48] | Meeeee, M.; Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[49] | Meeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M.; Meeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.