Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl3/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4H-carbazol-4-ones and Related Heterocycles,The Journal of Organic Chemistry

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Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl3/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4H-carbazol-4-ones and Related Heterocycles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-09-05 00:00:00 , DOI: 10.1021/acs.joc.8b01940
Yun Qiu ₁ , Michael Dlugosch ₂ , Xin Liu ₂ , Faiyaz Khan ₂ , Jas S. Ward ₂ , Ping Lan ₁ , Martin G. Banwell ₂

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Compounds such as 3, the product of a palladium[0]-catalyzed Ullmann cross-coupling of o-iodonitrobenzene and 2-iodocyclohex-2-en-1-one, undergo complementary modes of reductive cyclization depending upon the conditions employed. Thus, on treatment with hydrogen in the presence of palladium on carbon, the tetrahydrocarbazole 4 is formed, while reaction of the same substrate (3) with TiCl₃ in acetone affords the 1,2,3,9-tetrahydro-4H-carbazol-4-one 6.

中文翻译：

TiCl ₃ / HCl或Fe / HCl对邻硝基硝基化的α，β-不饱和醛和酮的还原环化反应生成1,2,3,9-四氢-4 H-咔唑-4-酮及相关杂环

化合物（3）是钯[0]催化的邻碘硝基苯和2-碘环己二烯-2-烯-1-酮的Ullmann交叉偶联产物，取决于所采用的条件，它们会经历互补的还原环化方式。因此，与在钯碳的存在下氢处理，四氢咔唑4的形成，而在同一基板（的反应3）用TiCl 4 ₃在丙酮中，得到1,2,3,9-四氢-4- ħ咔-4-一6。

更新日期：2018-09-05

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