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- W1976642823 abstract "A one-pot synthesis of azaheterocyclo[1,2,3-lm]-fused benzo[c]carbazoles (2 and 3) has been developed by photocyclization of 3-acyl-2-halo-1-[(ω-phenylethynyl)alkyl] indoles (1) in good to excellent yields. All products are formed from 1 via two sequential photocyclization reactions. Two products, 9-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2a-h) and 7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3a-h), are produced in the photocyclization of 2-halo-1-[(ω-phenylethynyl)alkyl]indole-3-carbaldehydes (1a-h). In contrast, only products 2a-h are produced in the photocyclization of 3-acetyl-2-chloro-1-[(ω-phenylethynyl)alkyl]indole-3-carbaldehydes (1o-t). The 9-H in 3a-h (n = 2) does originate from the formyl group in 1a-h via 1,5-hydrogen shift. The structures of three new products, 9-bromo-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2b), 9-chloro-10-methyl-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3h) and 12-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2w), have been corroborated by single-crystal X-ray structural analyses." @default.
- W1976642823 created "2016-06-24" @default.
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- W1976642823 date "2011-06-15" @default.
- W1976642823 modified "2023-09-23" @default.
- W1976642823 title "Photoinduced Cyclization of 3-Acyl-2-halo-1-[(ω-phenylethynyl)alkyl]indoles to Azaheterocyclo[1,2,3-<i>lm</i>]-Fused Benzo[<i>c</i>]carbazoles" @default.
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- W1976642823 doi "https://doi.org/10.1021/jo200630x" @default.
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