Catalyst-free anti-Markovnikov hydroamination and hydrothiolation of vinyl heteroarenes in aqueous medium: an improved process towards centhaquine
Catalyst-free hydroamination and hydrothiolation of alkenes have been achieved in an aqueous medium. The anti-Markovnikov addition works efficiently in suspended water at room temperature and allows straightforward access to centhaquine, a drug used for the management of hypovolemic shocks in critic...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2024-02, Vol.22 (8), p.1721-1726 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Yadav, Anamika Ambule, Mayur D Srivastava, Ajay Kumar |
| description | Catalyst-free hydroamination and hydrothiolation of alkenes have been achieved in an aqueous medium. The anti-Markovnikov addition works efficiently in suspended water at room temperature and allows straightforward access to centhaquine, a drug used for the management of hypovolemic shocks in critically ill patients, and its derivatives. Various primary and secondary amines, thiols, and hydrazides were successfully reacted with a number of heteroaryl/aryl-alkenes. The scalability of the process has been demonstrated by synthesizing centhaquine at a 19.65 g scale. A comparative analysis of the present process with previous approaches has been provided on the basis of green chemistry metrics.
Catalyst-free hydroamination and hydrothiolation of vinyl heteroarenes/electron deficient alkenes have been achieved in an aqueous medium. |
| doi_str_mv | 10.1039/d3ob02046k |
| format | Article |
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Catalyst-free hydroamination and hydrothiolation of vinyl heteroarenes/electron deficient alkenes have been achieved in an aqueous medium.</description><subject>Alkenes</subject><subject>Amines</subject><subject>Aqueous solutions</subject><subject>Catalysts</subject><subject>Comparative analysis</subject><subject>Green chemistry</subject><subject>Hydrazides</subject><subject>Room temperature</subject><subject>Thiols</subject><subject>Vadose water</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkU1P3DAQhq2qqMCWS--tLPWCkAL-yibmVpaPIqi4lHPk2BOtIbHBdhbt3-AX19vAVurFY8088-rVvAh9oeSYEi5PDPctYUTMHz-gPSqqqiAllx-3f0Z20X6MD4RQWc3FJ7TLa05rWYs99LpQSfXrmIouAGDlki1-qfDoV87mBy_XJng1WKeS9S7PzdRKS-v7qec7vLJu3eMlJMhwAAcR2ww_j-DHiAcwdhxO8zK2w1PwKzA4Fw0x4uRfVDARa3BpmResg89op1N9hIO3OkP3lxe_Fz-L27ur68WP20IzOU9FJaDitaFcA2eG0qrtTEUEGMapMKbjHeMlJUK3WpFSmFrLeSkN1Ea2StGSz9DhpJu9ZKcxNYONGvpeuY3thknGZFZgNKPf_0Mf_Bhcdreh6jpfVmyoo4nSwccYoGuegh1UWDeUNJukmnN-d_Y3qZsMf3uTHNt8oC36Hk0Gvk5AiHo7_Rc1_wNlB5v_</recordid><startdate>20240221</startdate><enddate>20240221</enddate><creator>Yadav, Anamika</creator><creator>Ambule, Mayur D</creator><creator>Srivastava, Ajay Kumar</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8463-7153</orcidid></search><sort><creationdate>20240221</creationdate><title>Catalyst-free anti-Markovnikov hydroamination and hydrothiolation of vinyl heteroarenes in aqueous medium: an improved process towards centhaquine</title><author>Yadav, Anamika ; Ambule, Mayur D ; Srivastava, Ajay Kumar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-74e738d13ce32d117bfd704ed2314ddf3f235104cbca054d8c9659de8d9baa153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkenes</topic><topic>Amines</topic><topic>Aqueous solutions</topic><topic>Catalysts</topic><topic>Comparative analysis</topic><topic>Green chemistry</topic><topic>Hydrazides</topic><topic>Room temperature</topic><topic>Thiols</topic><topic>Vadose water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yadav, Anamika</creatorcontrib><creatorcontrib>Ambule, Mayur D</creatorcontrib><creatorcontrib>Srivastava, Ajay Kumar</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yadav, Anamika</au><au>Ambule, Mayur D</au><au>Srivastava, Ajay Kumar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalyst-free anti-Markovnikov hydroamination and hydrothiolation of vinyl heteroarenes in aqueous medium: an improved process towards centhaquine</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-02-21</date><risdate>2024</risdate><volume>22</volume><issue>8</issue><spage>1721</spage><epage>1726</epage><pages>1721-1726</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Catalyst-free hydroamination and hydrothiolation of alkenes have been achieved in an aqueous medium. The anti-Markovnikov addition works efficiently in suspended water at room temperature and allows straightforward access to centhaquine, a drug used for the management of hypovolemic shocks in critically ill patients, and its derivatives. Various primary and secondary amines, thiols, and hydrazides were successfully reacted with a number of heteroaryl/aryl-alkenes. The scalability of the process has been demonstrated by synthesizing centhaquine at a 19.65 g scale. A comparative analysis of the present process with previous approaches has been provided on the basis of green chemistry metrics.
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-02, Vol.22 (8), p.1721-1726 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_pubmed_primary_38318984 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes Amines Aqueous solutions Catalysts Comparative analysis Green chemistry Hydrazides Room temperature Thiols Vadose water |
| title | Catalyst-free anti-Markovnikov hydroamination and hydrothiolation of vinyl heteroarenes in aqueous medium: an improved process towards centhaquine |
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