Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient...
| Authors: | ; ; ; |
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| Format: | Article |
| Status: | Published version |
| Publication date: | 2009 |
| Country: | Argentina |
| Institution: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repository: | CONICET Digital (CONICET) |
| Language: | English |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/26110 |
| Online Access: | http://hdl.handle.net/11336/26110 |
| Access Level: | Open access |
| Keyword: | Azaheterocycles Intramolecular Srn1 Pyrrole Indole https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| _version_ | 1878403174090407936 |
|---|---|
| author | Vaillard, Victoria Anahi |
| author2 | Buden, Maria Eugenia Martín, Sandra Elizabeth Rossi, Roberto Arturo |
| author2_role | author author author |
| author_browse | Buden, Maria Eugenia Martín, Sandra Elizabeth Rossi, Roberto Arturo Vaillard, Victoria Anahi |
| author_facet | Vaillard, Victoria Anahi Buden, Maria Eugenia Martín, Sandra Elizabeth Rossi, Roberto Arturo |
| author_role | author |
| collection | CONICET Digital (CONICET) |
| description | The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient two-step synthesis of new fused azaheterocycles derived from pyrrole, indole, and pyrazole, as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15a-b) with a base, the corresponding anion could be formed. Then, by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%). |
| eu_rights_str_mv | openAccess |
| format | article |
| id | AR_4c052d1fdcc7a106658da27878075f36 |
| identifier_str_mv | Vaillard, Victoria Anahi; Buden, Maria Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto Arturo; Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles; Elsevier; Tetrahedron Letters; 50; 27; 12-2009; 3829-3832 0040-4039 CONICET Digital CONICET |
| institution | Consejo Nacional de Investigaciones Científicas y Técnicas |
| instname_str | Consejo Nacional de Investigaciones Científicas y Técnicas |
| language | eng |
| network_acronym_str | AR |
| network_name_str | Argentina |
| oai_identifier_str | oai:ri.conicet.gov.ar:11336/26110 |
| publishDate | 2009 |
| publishDateSort | 2009 |
| publisher | Elsevier |
| publisherStr | Elsevier |
| reponame_str | CONICET Digital (CONICET) |
| spelling | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles Vaillard, Victoria Anahi Buden, Maria Eugenia Martín, Sandra Elizabeth Rossi, Roberto Arturo Azaheterocycles Intramolecular Srn1 Pyrrole Indole https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient two-step synthesis of new fused azaheterocycles derived from pyrrole, indole, and pyrazole, as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15a-b) with a base, the corresponding anion could be formed. Then, by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%). Fil: Vaillard, Victoria Anahi. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Rossi, Roberto Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Elsevier http://hdl.handle.net/11336/26110 Vaillard, Victoria Anahi; Buden, Maria Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto Arturo; Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles; Elsevier; Tetrahedron Letters; 50; 27; 12-2009; 3829-3832 0040-4039 CONICET Digital CONICET |
| spellingShingle | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles Vaillard, Victoria Anahi Azaheterocycles Intramolecular Srn1 Pyrrole Indole https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| status_str | publishedVersion |
| title | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| title_full | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| title_fullStr | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| title_full_unstemmed | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| title_short | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| title_sort | Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles |
| topic | Azaheterocycles Intramolecular Srn1 Pyrrole Indole https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| topic_facet | Azaheterocycles Intramolecular Srn1 Pyrrole Indole https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| url | http://hdl.handle.net/11336/26110 |