One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives
The development of sustainable methods is highly desirable in synthetic organic chemistry. In this regard, we report hydroxylamine hydrochloride mediated, one-pot synthesis of 1,3-diazaheterocycles using anthranilamide or o-phenylenediamine with amides via transamidation under solvent free condition...
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| Veröffentlicht in: | Tetrahedron 2024-03, Vol.154, p.133866, Article 133866 |
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| creator | Shaik, Baji Baba Mohite, Sachin Balaso Partap, Sangh Kumar, Vishal Vangara, Srinivas Bala, Muhammad Dabai Singh, Parvesh Karpoormath, Rajshekhar |
| description | The development of sustainable methods is highly desirable in synthetic organic chemistry. In this regard, we report hydroxylamine hydrochloride mediated, one-pot synthesis of 1,3-diazaheterocycles using anthranilamide or o-phenylenediamine with amides via transamidation under solvent free condition at 120–140 °C for 8–14 h. This method proceeds smoothly under metal- and oxidant-free conditions exhibited broad substrate scope with reference to both diamines derivatives and amides, resulted in corresponding 4(3H)-quinazolinone (3) and benzimidazoles (5&6) (∼47 examples) in good to excellent yield (56–96 %). As an efficient and environmentally friendly access to a broad range of 4(3H)-quinazolinones and benzimidazoles and the synthetic utility of this method was demonstrated by gram-scale operation, achieved >90 % yield.
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| doi_str_mv | 10.1016/j.tet.2024.133866 |
| format | Article |
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[Display omitted]</description><subject>1,3-Diazaheterocycles</subject><subject>amides</subject><subject>Anthranilamide</subject><subject>Benzimidazoles</subject><subject>diamines</subject><subject>hydroxylamine</subject><subject>Hydroxylamine hydrochloride</subject><subject>organic chemistry</subject><subject>Solvent-free</subject><subject>solvents</subject><subject>synthesis</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kL1u2zAUhYkgAeIkfYBuGjtE9iUpUTY6FW7zAzjwkswETV5BNGTSJRkjyjv0nUNFnTNdXOB8BzgfId8pzClQsdjPE6Y5A1bNKedLIc7IjFaiKuuKinMyA6igrIDBJbmKcQ8AlDI-I_-2DsujT0UcXOow2lj4tqC3vDRWvasOEwavB91jLE5WFd1ggn8benWwDqdPd70P1mChdLInlax3Y4fKfUE5O0YNLo4duqFHh7l3ZGMOmOL3011hMHxiJ4w35KJVfcRv_-81ebn787x-KDfb-8f1r02p2ZKlUtVMVA1faWqaFeVtw5agFW-13lGuzRJE00C74oIp2K12TYO1MaZiO2W0aTN5TX5Mvcfg_75iTPJgo8a-Vw79a5Sc1lwA1AA5SqeoDj7GgK08BntQYZAU5Khe7mVWL0f1clKfmZ8Tg3nDyWKQUVt0Om8PqJM03n5BfwBrI4_2</recordid><startdate>20240325</startdate><enddate>20240325</enddate><creator>Shaik, Baji Baba</creator><creator>Mohite, Sachin Balaso</creator><creator>Partap, Sangh</creator><creator>Kumar, Vishal</creator><creator>Vangara, Srinivas</creator><creator>Bala, Muhammad Dabai</creator><creator>Singh, Parvesh</creator><creator>Karpoormath, Rajshekhar</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-1247-5754</orcidid></search><sort><creationdate>20240325</creationdate><title>One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives</title><author>Shaik, Baji Baba ; Mohite, Sachin Balaso ; Partap, Sangh ; Kumar, Vishal ; Vangara, Srinivas ; Bala, Muhammad Dabai ; Singh, Parvesh ; Karpoormath, Rajshekhar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-a5264739c1d7913f7280ca3fccb13cd806770f9362a0b9b77e5ddd42badcdf473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>1,3-Diazaheterocycles</topic><topic>amides</topic><topic>Anthranilamide</topic><topic>Benzimidazoles</topic><topic>diamines</topic><topic>hydroxylamine</topic><topic>Hydroxylamine hydrochloride</topic><topic>organic chemistry</topic><topic>Solvent-free</topic><topic>solvents</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shaik, Baji Baba</creatorcontrib><creatorcontrib>Mohite, Sachin Balaso</creatorcontrib><creatorcontrib>Partap, Sangh</creatorcontrib><creatorcontrib>Kumar, Vishal</creatorcontrib><creatorcontrib>Vangara, Srinivas</creatorcontrib><creatorcontrib>Bala, Muhammad Dabai</creatorcontrib><creatorcontrib>Singh, Parvesh</creatorcontrib><creatorcontrib>Karpoormath, Rajshekhar</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shaik, Baji Baba</au><au>Mohite, Sachin Balaso</au><au>Partap, Sangh</au><au>Kumar, Vishal</au><au>Vangara, Srinivas</au><au>Bala, Muhammad Dabai</au><au>Singh, Parvesh</au><au>Karpoormath, Rajshekhar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives</atitle><jtitle>Tetrahedron</jtitle><date>2024-03-25</date><risdate>2024</risdate><volume>154</volume><spage>133866</spage><pages>133866-</pages><artnum>133866</artnum><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>The development of sustainable methods is highly desirable in synthetic organic chemistry. In this regard, we report hydroxylamine hydrochloride mediated, one-pot synthesis of 1,3-diazaheterocycles using anthranilamide or o-phenylenediamine with amides via transamidation under solvent free condition at 120–140 °C for 8–14 h. This method proceeds smoothly under metal- and oxidant-free conditions exhibited broad substrate scope with reference to both diamines derivatives and amides, resulted in corresponding 4(3H)-quinazolinone (3) and benzimidazoles (5&6) (∼47 examples) in good to excellent yield (56–96 %). As an efficient and environmentally friendly access to a broad range of 4(3H)-quinazolinones and benzimidazoles and the synthetic utility of this method was demonstrated by gram-scale operation, achieved >90 % yield.
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| subjects | 1,3-Diazaheterocycles amides Anthranilamide Benzimidazoles diamines hydroxylamine Hydroxylamine hydrochloride organic chemistry Solvent-free solvents synthesis |
| title | One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives |
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