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Versatile Access to C-4-Substituted 2-Amino-1,3-azoles from Hydropyridines in Oxidative Conditions
Various substituted 2-aminotetrahydroazolopyridines and 2-aminohexahydroazolopyridines have been prepared by bromine-mediated addition of protected guanidine or urea to hydropyridine derivatives. The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole produc...
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| Published in: | Journal of organic chemistry 2005-09, Vol.70 (20), p.8208-8211 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a381t-3d4a82df13ef2fbb49c4a468402d8b4ca16d15988bd29b72ec619d3e6baacc203 |
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| cites | cdi_FETCH-LOGICAL-a381t-3d4a82df13ef2fbb49c4a468402d8b4ca16d15988bd29b72ec619d3e6baacc203 |
| container_end_page | 8211 |
| container_issue | 20 |
| container_start_page | 8208 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | del Rayo Sanchez Salvatori, Maria Abou-Jneid, Robert Ghoulami, Saïd Martin, Marie-Thérèse Zaparucha, Anne Al-Mourabit, Ali |
| description | Various substituted 2-aminotetrahydroazolopyridines and 2-aminohexahydroazolopyridines have been prepared by bromine-mediated addition of protected guanidine or urea to hydropyridine derivatives. The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole products III. The yields of the bicycles of type II, and their conversion into azoles III depends on the electronic properties of the substituents on the nitrogen of the tetrahydopyridine. |
| doi_str_mv | 10.1021/jo050862o |
| format | article |
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The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole products III. 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The yields of the bicycles of type II, and their conversion into azoles III depends on the electronic properties of the substituents on the nitrogen of the tetrahydopyridine.</description><subject>Amines - chemistry</subject><subject>Azoles - chemistry</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Kinetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Pyridines - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpt0F1rFDEUBuAgil2rF_4BmRsFwWi-JslcLutHLdWKrd6GTJKB1JnJNicjXX-9kV26N56bwMnDy-FF6Dklbylh9N1NIi3RkqUHaEVbRrDsiHiIVoQwhjmT_AQ9Abghddq2fYxOqGRK8ZauUP8zZLAljqFZOxcAmpKaDRb4aumhxLKU4BuG11OcE6ZvOLZ_0higGXKamrOdz2m7y9HHue7i3FzeRV_Tfodmk2YfS0wzPEWPBjtCeHZ4T9GPjx-uN2f44vLT5836AluuacHcC6uZHygPAxv6XnROWCG1IMzrXjhLpadtp3XvWdcrFpyknedB9tY6xwg_Ra_2uducbpcAxUwRXBhHO4e0gJFaKSk6VeHrPXQ5AeQwmG2Ok807Q4n5V6i5L7TaF4fQpZ-CP8pDgxW8PAALzo5DtrOLcHSKCqU5rw7vXYQS7u7_bf5lpOKqNdffrsyXc_b9_D0T5usx1zqo9yx5rt3958C__vyYnA</recordid><startdate>20050930</startdate><enddate>20050930</enddate><creator>del Rayo Sanchez Salvatori, Maria</creator><creator>Abou-Jneid, Robert</creator><creator>Ghoulami, Saïd</creator><creator>Martin, Marie-Thérèse</creator><creator>Zaparucha, Anne</creator><creator>Al-Mourabit, Ali</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050930</creationdate><title>Versatile Access to C-4-Substituted 2-Amino-1,3-azoles from Hydropyridines in Oxidative Conditions</title><author>del Rayo Sanchez Salvatori, Maria ; Abou-Jneid, Robert ; Ghoulami, Saïd ; Martin, Marie-Thérèse ; Zaparucha, Anne ; Al-Mourabit, Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-3d4a82df13ef2fbb49c4a468402d8b4ca16d15988bd29b72ec619d3e6baacc203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amines - chemistry</topic><topic>Azoles - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Kinetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Pyridines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>del Rayo Sanchez Salvatori, Maria</creatorcontrib><creatorcontrib>Abou-Jneid, Robert</creatorcontrib><creatorcontrib>Ghoulami, Saïd</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Zaparucha, Anne</creatorcontrib><creatorcontrib>Al-Mourabit, Ali</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>del Rayo Sanchez Salvatori, Maria</au><au>Abou-Jneid, Robert</au><au>Ghoulami, Saïd</au><au>Martin, Marie-Thérèse</au><au>Zaparucha, Anne</au><au>Al-Mourabit, Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Versatile Access to C-4-Substituted 2-Amino-1,3-azoles from Hydropyridines in Oxidative Conditions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| ispartof | Journal of organic chemistry, 2005-09, Vol.70 (20), p.8208-8211 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Amines - chemistry Azoles - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Kinetics Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Organic chemistry Oxidation-Reduction Preparations and properties Pyridines - chemistry |
| title | Versatile Access to C-4-Substituted 2-Amino-1,3-azoles from Hydropyridines in Oxidative Conditions |
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