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1-Alkyl-5-((di)alkylamino) Tetrazoles: Building Blocks for Peptide Surrogates
An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in bot...
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| Published in: | Journal of organic chemistry 2012-01, Vol.77 (2), p.1174-1180 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a344t-9ddd521c56a0c9f3893deba6fd51ecde9b1391bd44b0505236cf0c751df638a33 |
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| cites | cdi_FETCH-LOGICAL-a344t-9ddd521c56a0c9f3893deba6fd51ecde9b1391bd44b0505236cf0c751df638a33 |
| container_end_page | 1180 |
| container_issue | 2 |
| container_start_page | 1174 |
| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Tymtsunik, Andriy V Bilenko, Vitaliy A Kokhan, Serhiy O Grygorenko, Oleksandr O Volochnyuk, Dmitriy M Komarov, Igor V |
| description | An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in both components of the reaction was demonstrated. Obtained tetrazoles are promising building blocks for the design of peptide surrogates, in particular, for replacement approaches of alkyl urea derivatives. |
| doi_str_mv | 10.1021/jo2022235 |
| format | article |
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Org. Chem</addtitle><date>2012-01-20</date><risdate>2012</risdate><volume>77</volume><issue>2</issue><spage>1174</spage><epage>1180</epage><pages>1174-1180</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in both components of the reaction was demonstrated. Obtained tetrazoles are promising building blocks for the design of peptide surrogates, in particular, for replacement approaches of alkyl urea derivatives.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22171684</pmid><doi>10.1021/jo2022235</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2012-01, Vol.77 (2), p.1174-1180 |
| 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 Chemistry Chemistry Techniques, Synthetic Drug Design Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Peptides Peptides - chemistry Preparations and properties Sulfinic Acids - chemistry Tetrazoles - chemical synthesis Tetrazoles - chemistry Urea - chemistry |
| title | 1-Alkyl-5-((di)alkylamino) Tetrazoles: Building Blocks for Peptide Surrogates |
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