Cyclization of 2,4‐dinitronaphth‐1‐yl amino acids and their analogues to naphthimindazol‐N‐oxides: Kinetics and mechanism
A variety of novel naphthimindazol‐N‐oxides and naphththiazol‐N‐oxide have been prepared in a simple two‐step process. The first step involves the reaction of 1‐chloro‐2,4‐dinitronaphthalene with glycine, alanine, glycolic acid, thioglycolic acid, and their methyl esters affording substitution produ...
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| Veröffentlicht in: | Journal of physical organic chemistry 2024-01, Vol.37 (1), p.n/a |
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| container_title | Journal of physical organic chemistry |
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| creator | Omar, Alaa Z. Khattab, Sherine N. Ibrahim, Mahmoud F. El‐Sadany, Samir K. Hamed, Ezzat A. |
| description | A variety of novel naphthimindazol‐N‐oxides and naphththiazol‐N‐oxide have been prepared in a simple two‐step process. The first step involves the reaction of 1‐chloro‐2,4‐dinitronaphthalene with glycine, alanine, glycolic acid, thioglycolic acid, and their methyl esters affording substitution products, the subsequent treatment of which with base furnishes naphthimindazol‐N‐oxide and naphththiazol‐N‐oxide derivatives. Stepwise reaction mechanisms via carbanions, nitrogen anions, and spiro Meisenheimer intermediates are proposed. The action of 10% NaOH in dioxane on the substitution products was measured spectrophotochemically, and the kinetic studies suggested that the N‐naphthyl glycine and N‐naphthyl alanine follow a second‐order rate law while S‐naphthyl thioglycolic acid is accurately first‐order kinetics.
Reaction of 1‐chloro‐2,4‐dinitronaphthalene with amino acids and their methyl esters. |
| doi_str_mv | 10.1002/poc.4568 |
| format | Article |
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Reaction of 1‐chloro‐2,4‐dinitronaphthalene with amino acids and their methyl esters.</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.4568</identifier><language>eng</language><publisher>Bognor Regis: Wiley Subscription Services, Inc</publisher><subject>Alanine ; Amino acids ; Esters ; Glycine ; Glycolic acid ; imidazol‐N‐oxide ; Kinetics ; Meisenheimer ; Nitrogen ; Reaction mechanisms ; second order ; Substitution reactions ; UV spectra</subject><ispartof>Journal of physical organic chemistry, 2024-01, Vol.37 (1), p.n/a</ispartof><rights>2023 John Wiley & Sons Ltd.</rights><rights>2024 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2888-b1e4fa6ad411966e394b2793d8214bda9d5c48dafe2edf6c66c89058fe232eee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpoc.4568$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpoc.4568$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Omar, Alaa Z.</creatorcontrib><creatorcontrib>Khattab, Sherine N.</creatorcontrib><creatorcontrib>Ibrahim, Mahmoud F.</creatorcontrib><creatorcontrib>El‐Sadany, Samir K.</creatorcontrib><creatorcontrib>Hamed, Ezzat A.</creatorcontrib><title>Cyclization of 2,4‐dinitronaphth‐1‐yl amino acids and their analogues to naphthimindazol‐N‐oxides: Kinetics and mechanism</title><title>Journal of physical organic chemistry</title><description>A variety of novel naphthimindazol‐N‐oxides and naphththiazol‐N‐oxide have been prepared in a simple two‐step process. The first step involves the reaction of 1‐chloro‐2,4‐dinitronaphthalene with glycine, alanine, glycolic acid, thioglycolic acid, and their methyl esters affording substitution products, the subsequent treatment of which with base furnishes naphthimindazol‐N‐oxide and naphththiazol‐N‐oxide derivatives. Stepwise reaction mechanisms via carbanions, nitrogen anions, and spiro Meisenheimer intermediates are proposed. The action of 10% NaOH in dioxane on the substitution products was measured spectrophotochemically, and the kinetic studies suggested that the N‐naphthyl glycine and N‐naphthyl alanine follow a second‐order rate law while S‐naphthyl thioglycolic acid is accurately first‐order kinetics.
Reaction of 1‐chloro‐2,4‐dinitronaphthalene with amino acids and their methyl esters.</description><subject>Alanine</subject><subject>Amino acids</subject><subject>Esters</subject><subject>Glycine</subject><subject>Glycolic acid</subject><subject>imidazol‐N‐oxide</subject><subject>Kinetics</subject><subject>Meisenheimer</subject><subject>Nitrogen</subject><subject>Reaction mechanisms</subject><subject>second order</subject><subject>Substitution reactions</subject><subject>UV spectra</subject><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kE1OwzAQhS0EEqUgcQRLbFiQ4r-kNjtU8ScqygLWlms7xFUShzgVpCskLsAZOQkuYctiNPM03xuNHgDHGE0wQuS88XrC0ozvgBFGQiSYinQXjBAXLKGEon1wEMIKobhLpyPwOet16Taqc76GPofkjH1_fBlXu671tWqKrogax-pLqCpXe6i0MwGq2sCusK6Nkyr9y9oG2Hk4WFwEjdr4MvoeYvl3Z2y4gPeutp3Tg7uyulC1C9Uh2MtVGezRXx-D5-urp9ltMl_c3M0u54kmnPNkiS3LVaYMw1hkmaWCLclUUMMJZkujhEk140bllliTZzrLNBco5VFTYq2lY3Ay3G1a_xr_7eTKr9v4fZBEYIpwyjmL1OlA6daH0NpcNq2rVNtLjOQ2YhkjltuII5oM6Jsrbf8vJx8Xs1_-BwCshAs</recordid><startdate>202401</startdate><enddate>202401</enddate><creator>Omar, Alaa Z.</creator><creator>Khattab, Sherine N.</creator><creator>Ibrahim, Mahmoud F.</creator><creator>El‐Sadany, Samir K.</creator><creator>Hamed, Ezzat A.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202401</creationdate><title>Cyclization of 2,4‐dinitronaphth‐1‐yl amino acids and their analogues to naphthimindazol‐N‐oxides: Kinetics and mechanism</title><author>Omar, Alaa Z. ; Khattab, Sherine N. ; Ibrahim, Mahmoud F. ; El‐Sadany, Samir K. ; Hamed, Ezzat A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2888-b1e4fa6ad411966e394b2793d8214bda9d5c48dafe2edf6c66c89058fe232eee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alanine</topic><topic>Amino acids</topic><topic>Esters</topic><topic>Glycine</topic><topic>Glycolic acid</topic><topic>imidazol‐N‐oxide</topic><topic>Kinetics</topic><topic>Meisenheimer</topic><topic>Nitrogen</topic><topic>Reaction mechanisms</topic><topic>second order</topic><topic>Substitution reactions</topic><topic>UV spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Omar, Alaa Z.</creatorcontrib><creatorcontrib>Khattab, Sherine N.</creatorcontrib><creatorcontrib>Ibrahim, Mahmoud F.</creatorcontrib><creatorcontrib>El‐Sadany, Samir K.</creatorcontrib><creatorcontrib>Hamed, Ezzat A.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Omar, Alaa Z.</au><au>Khattab, Sherine N.</au><au>Ibrahim, Mahmoud F.</au><au>El‐Sadany, Samir K.</au><au>Hamed, Ezzat A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cyclization of 2,4‐dinitronaphth‐1‐yl amino acids and their analogues to naphthimindazol‐N‐oxides: Kinetics and mechanism</atitle><jtitle>Journal of physical organic chemistry</jtitle><date>2024-01</date><risdate>2024</risdate><volume>37</volume><issue>1</issue><epage>n/a</epage><issn>0894-3230</issn><eissn>1099-1395</eissn><abstract>A variety of novel naphthimindazol‐N‐oxides and naphththiazol‐N‐oxide have been prepared in a simple two‐step process. The first step involves the reaction of 1‐chloro‐2,4‐dinitronaphthalene with glycine, alanine, glycolic acid, thioglycolic acid, and their methyl esters affording substitution products, the subsequent treatment of which with base furnishes naphthimindazol‐N‐oxide and naphththiazol‐N‐oxide derivatives. Stepwise reaction mechanisms via carbanions, nitrogen anions, and spiro Meisenheimer intermediates are proposed. The action of 10% NaOH in dioxane on the substitution products was measured spectrophotochemically, and the kinetic studies suggested that the N‐naphthyl glycine and N‐naphthyl alanine follow a second‐order rate law while S‐naphthyl thioglycolic acid is accurately first‐order kinetics.
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | Alanine Amino acids Esters Glycine Glycolic acid imidazol‐N‐oxide Kinetics Meisenheimer Nitrogen Reaction mechanisms second order Substitution reactions UV spectra |
| title | Cyclization of 2,4‐dinitronaphth‐1‐yl amino acids and their analogues to naphthimindazol‐N‐oxides: Kinetics and mechanism |
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