{"product_id":"9783832543976","title":"Sulfonyl Ynamides as Useful Tools for N-Heterocyclic Chemistry","description":"\u003cp\u003eSulfonyl ynamides are highly versatile and synthetically useful reagents. This thesis details the modular synthesis and use of sulfonyl ynamides in order to access N-heterocyclic scaffolds, such as quinolines and pyrazoles. The synthesis of a wide array of sulfonyl ynamides can be realized via copper-catalyzed amidative cross-couplings or by elimination of dichloroenamide precursors. Additionally the use of Sonogashira chemistry to further diversify terminal ynamides and the synthesis of solid-supported ynamides was investigated. Electrophilically-activated amides can be reacted with sulfonyl ynamides in order to access highly functionalized 4-aminoquinolines. The straightforward amide activation procedure with triflic anhydride and 2-chloropyridine was found to tolerate a wide range of substrates, which allowed for the development of a library of 4-aminoquinolines with ease. Moreover, 4-aminopyrazoles can be prepared by reacting terminal sulfonyl ynamides with sydnones under copper catalysis. However, as the copper catalysts were also found to promote the degradation of the ynamides, a copper-free strain-promoted alternative was developed. An in situ prepared 3-azacyclohexyne was found to tolerate a wide array of C-4 substituted sydnones, producing a mixture of both the 3,4- and 4,3-fused pyrazoles in good yields. Additional investigations into heterocyclic methodology led to the development of highly sophisticated, non-symmetrical and axially-chiral dibenzo-1,3-diazepines, -oxazepines and -thiazepines from simple, commercially available anilines. The anilines were coupled to their corresponding reaction partners via a chloromethyl intermediate and the 7-membered ring was subsequently formed using direct arylation.\u003c\/p\u003e","brand":"Logos Verlag Berlin","offers":[{"title":"Default Title","offer_id":47035627143408,"sku":"9783832543976","price":58.0,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0737\/7593\/9824\/files\/9783832543976_p0.jpg?v=1763687626","url":"https:\/\/shop-qa.barnesandnoble.com\/products\/9783832543976","provider":"Barnes \u0026 Noble (DEV)","version":"1.0","type":"link"}