Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles
The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1<i>H</i>-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1<i>H</i>-indole byproducts. Herein, we off...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-10-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/20/6132 |
| _version_ | 1827679014521667584 |
|---|---|
| author | Alexander V. Aksenov Nicolai A. Aksenov Elena V. Aleksandrova Dmitrii A. Aksenov Igor Yu. Grishin Elena A. Sorokina Allison Wenger Michael Rubin |
| author_facet | Alexander V. Aksenov Nicolai A. Aksenov Elena V. Aleksandrova Dmitrii A. Aksenov Igor Yu. Grishin Elena A. Sorokina Allison Wenger Michael Rubin |
| author_sort | Alexander V. Aksenov |
| collection | DOAJ |
| description | The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1<i>H</i>-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1<i>H</i>-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules. |
| first_indexed | 2024-03-10T06:20:52Z |
| format | Article |
| id | doaj.art-2c77222fc40348e79d1e7a14e4afc9e7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:20:52Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2c77222fc40348e79d1e7a14e4afc9e72023-11-22T19:18:31ZengMDPI AGMolecules1420-30492021-10-012620613210.3390/molecules26206132Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)AcetonitrilesAlexander V. Aksenov0Nicolai A. Aksenov1Elena V. Aleksandrova2Dmitrii A. Aksenov3Igor Yu. Grishin4Elena A. Sorokina5Allison Wenger6Michael Rubin7Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaDepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaOrganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya St., 117198 Moscow, RussiaDepartment of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, USADepartment of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, RussiaThe recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1<i>H</i>-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1<i>H</i>-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules.https://www.mdpi.com/1420-3049/26/20/6132nitroalkanesheterocycles1,2-alkyl shiftrearrangementscascade transformations |
| spellingShingle | Alexander V. Aksenov Nicolai A. Aksenov Elena V. Aleksandrova Dmitrii A. Aksenov Igor Yu. Grishin Elena A. Sorokina Allison Wenger Michael Rubin Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles Molecules nitroalkanes heterocycles 1,2-alkyl shift rearrangements cascade transformations |
| title | Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles |
| title_full | Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles |
| title_fullStr | Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles |
| title_full_unstemmed | Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles |
| title_short | Direct Conversion of 3-(2-Nitroethyl)-1<i>H</i>-Indoles into 2-(1<i>H</i>-Indol-2-yl)Acetonitriles |
| title_sort | direct conversion of 3 2 nitroethyl 1 i h i indoles into 2 1 i h i indol 2 yl acetonitriles |
| topic | nitroalkanes heterocycles 1,2-alkyl shift rearrangements cascade transformations |
| url | https://www.mdpi.com/1420-3049/26/20/6132 |
| work_keys_str_mv | AT alexandervaksenov directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT nicolaiaaksenov directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT elenavaleksandrova directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT dmitriiaaksenov directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT igoryugrishin directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT elenaasorokina directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT allisonwenger directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles AT michaelrubin directconversionof32nitroethyl1ihiindolesinto21ihiindol2ylacetonitriles |