- One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
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A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
- Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
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supporting information
p. 6127 - 6140
(2021/07/21)
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- Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
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Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
- O'Brien, Keith,ó Proinsias, Keith,Kelleher, Fintan
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supporting information
p. 5082 - 5092
(2014/07/08)
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- Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
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Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
- O'Brien, Keith,ó Proinsias, Keith,Kelleher, Fintan
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supporting information
p. 5082 - 5092
(2014/12/10)
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- Nickel-catalyzed regio- and enantioselective annulation reactions of 1,2,3,4-benzothiatriazine-1,1(2H)-dioxides with allenes
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(Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline.
- Miura, Tomoya,Yamauchi, Motoshi,Kosaka, Akira,Murakami, Masahiro
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supporting information; experimental part
p. 4955 - 4957
(2010/10/02)
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- The facile preparation of primary and secondary amines via an improved Fukuyama-Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent
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An efficient modification of the Fukuyama-Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved technique was implemented in the synthesis of a complex lipopeptide designed to target α 9β1-integrin proteins predominant on upper airway epithelial cells. The Royal Society of Chemistry 2005.
- Guisado, Cristina,Waterhouse, Jodie E.,Price, Wayne S.,Jorgensen, Michael R.,Miller, Andrew D.
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p. 1049 - 1057
(2007/10/03)
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- Alkyne matrix metalloproteinase inhibitors
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A compound of Formula I or a pharmaceutically acceptable salt thereof, or a tautomer thereof, wherein G1, G2, and B are as defined in the application, are selective inhibitors of MMP-13. The compounds are useful for treating diseases mediated by MMP-13, including cancer and arthritis.
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- New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
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A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd.
- Barrett, Stephen,O'Brien, Peter,Steffens, H.Christian,Towers, Timothy D,Voith, Matthias
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p. 9633 - 9640
(2007/10/03)
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- 2- and 4-Nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines
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2- and 4-nitrobenzenesulfonamides, readily prepared from primary amines, undergo smooth alkylation by Mitsunobu reaction or by conventional methods to give N-alkylated sulfonamides in near quantitative yields. These sulfonamides could be deprotected readily via Meisenheimer complexes upon treatment with thiolates in DMF at room temperature, giving secondary amines in high yields.
- Fukuyama, Tohru,Jow, Chung-Kuang,Cheung, Mui
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p. 6373 - 6374
(2007/10/02)
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