Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 12
400
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Solid-Phase Synthesis of N-Aryl Succinimides

&
Pages 2108-2115 | Received 11 Sep 2008, Published online: 13 May 2009

REFERENCES

  • Czarnik , A. W. (Ed.) Solid-Phase Organic Synthesis ; Wiley : New York , 2001 .
  • Krchnak , V. ; Holladay , M. W. Solid-phase heterocyclic chemistry . Chem. Rev. 2002 , 102 , 61 – 91 .
  • Blaney , P. ; Grigg , R. ; Sridharan , V. Traceless solid-phase organic synthesis . Chem. Rev. 2002 , 102 , 2607 – 2624 .
  • Franzén , R. G. Recent advances in the preparation of heterocycles on solid support . J. Comb. Chem. 2000 , 2 , 195 – 214 .
  • Dolle , R. E. Comprehensive survey of combinatorial library synthesis . J. Comb. Chem. 2004 , 6 , 623 – 679 .
  • Zaragoza Dorwald , F. Organic Syntheses on Solid Phase ; Wiley-VCH : Weinheim , 2000 .
  • Guillier , F. ; Orain , D. ; Bradley , M. Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry . Chem. Rev. 2000 , 100 , 2091 – 2157 .
  • Lebl , M. In Integrated Drug Discovery Technologies ; H.-Y. Mei , and A. W. Czarnik , (Eds.); Marcel Dekker : New York , 2002; 395–405.
  • Gordon , E. M. ; Barrett , R. W. ; Dower , W. J. ; Foder , S. P. A. ; Gallop , M. A. Application of combinatorial technologies to drug discovery . J. Med. Chem. 1994 , 37 , 1385 – 1401 .
  • Nicolaou , K. C. ; Hanko , R. ; Hartwig , W. (Eds.) Handbook of Combinatorial Chemistry ; Wiley-VCH : Weinheim , 2002 ; vols. 1–2 .
  • Timofte , R. S. ; Titman , J. J. ; Shao , L. ; Stephens , J. C. ; Woodward , S. Investigations into the utility of high-surface-area silica pellets as potential solid-phase synthesis supports . Tetrahedron 2005 , 61 , 51 – 59 .
  • Keana , J. F. W. ; Shimizu , M. ; Jernstedt , K. K. Functionalized silica gel as a support for solid-phase organic synthesis . J. Org. Chem. 1986 , 51 , 1641 – 1644 .
  • Carpino , L. A. ; Mansour , E. M. E. ; Knapczyk , J. Piperazino-functionalized silica gel as a deblocking-scavenging agent for the 9-fluorenylmethyloxycarbonyl amino-protecting group . J. Org. Chem. 1983 , 48 , 666 – 669 .
  • Tanimori , S. ; Sunami , T. ; Fukubayashi , K. ; Kirihata , M. An efficient construction of bridged chiral tetracyclic indolidines, a core structure of asperparaline, via stereocontrolled catalytic Pauson–Khand reaction . Tetrahedron 2005 , 61 , 2481 – 2492 .
  • Marson , C. M. ; Pink , J. H. ; Smith , C. Synthesis of the first monoaromatic B-ring 13-azasteroid ring system by sequential angular annulation . Tetrahedron 2003 , 59 , 10019 – 10023 .
  • Hargreaves , M. K. ; Pritchard , J. G. ; Dave , H. R. Cyclic carboxylic monoimides . Chem. Rev. 1970 , 70 , 439 – 469 .
  • Curtin , M. L. ; Garland , R. B. ; Heyman , H. R. ; Frey , R. R. ; Michaelides , M. R. ; Li , J. ; Pease , L. J. ; Glaser , K. B. ; Marcotte , P. A. ; Davidsen , S. K. Succinimide hydroxamic acids as potent inhibitors of histone deacetylase . Bioorg. Med. Chem. Lett. 2002 , 12 , 2919 – 2923 .
  • Abell , A. D. ; Oldham , M. D. Synthesis and x-ray crystallographic structure of leucine-phenylalanyl succinimide-based pseudopeptides . J. Org. Chem. 1997 , 62 , 1509 – 1513 .
  • Zajdel , P. ; Subra , G. ; Bojarski , A. J. ; Duszynska , B. ; Tatarczynska , E. ; Nikiforuk , A. ; Chojnacka-Wojcik , E. ; Pawlowski , M. ; Martinez , J. Novel class of arylpiperazines containing N-acylated amino acids: Their syntheis, 5-HT1A, 5-HT2A receptor affinity, and in vivo pharmacological evaluation . Bioorg. Med. Chem. 2007 , 15 , 2907 – 2919 .
  • Briere , J.-F. ; Charpentier , P. ; Dupas , G. ; Queguiner , G. ; Bourguignon , J. Regioselecive reduction of various 3-aminosuccinimides: Application to the synthesis of two heterocyclic systems . Tetrahedron 1997 , 53 , 2075 – 2086 .
  • Reddy , P. Y. ; Kondo , S. ; Toru , T. ; Ueno , Y. Lewis acid and hexamethyldisilazane-promoted efficient synthesis of N-alkyl- and N-arylimide derivatives . J. Org. Chem. 1997 , 62 , 2652 – 2654 .
  • Katritzky , A. R. ; Nair , S. K. ; Witek , R. M. ; Hutchins , S. M. Synthesis of 3,3-diarylpyrrolidines from diaryl ketones . Arkivoc 2003 , 5 , 9 – 18 .
  • Lebrun , S. ; Couture , A. ; Deniau , E. ; Grandclaudon , P. Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines. Tetrahedron: Asymmetry 2003, 14, 2625–2632.
  • Quiroz , T. ; Corona , D. ; Covarruvias , A. ; Avila-Zarraga , J. G. ; Romero-Ortega , M. A practical method for the synthesis of pyrrolizidine, indolizidine, and pyrroloazepinolizidine nucleus . Tetrahedron Lett. 2007 , 48 , 1571 – 1575 .
  • Alvarez-Gutierrez , J. M. ; Nefzi , A. ; Houghten , R. A. Solid phase synthesis of 1,3-disubstituted succinimides . Tetrahedron Lett. 2000 , 41 , 609 – 612 .
  • Haval , K. P. ; Mhaske , S. B. ; Argade , N. P. Cyanuric chloride: Decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides . Tetrahedron 2006 , 62 , 937 – 942 .
  • Mohanazadeh , F. ; Momeni , A. R. ; Ranjbar , Y. Deoxygenation of sulfoxides with silica chloride . Tetrahedron Lett. 1994 , 35 , 6127 – 6128 .
  • Srinivas , K. V. N. S. ; Mahender , I. ; Das , B. Silica chloride: A versatile heterogeneous catalyst for esterification and transesterification . Synthesis 2003 , 2390 – 2394 .
  • Mirjalili , B. ; Pourjavadi , A. ; Zolfigol , M. A. ; Bamoniri , A. Silica chloride/wet SiO2 as a novel heterogeneous system for the deprotection of acetals under mild conditions . Phosphorus, Sulfur Silicon Relat. Elem. 2003 , 178 , 2667 – 2670 .
  • Sathe , M. ; Kaushik , M. P. An efficient method for the esterification of amino acids using silica chloride . Catal. Commun. 2006 , 7 , 644 – 646 .
  • Kamitori , Y. ; Hojo , M. ; Masuda , R. ; Kimura , T. ; Yoshida , T. Selective protection of carbonyl compounds: Silica gel treated with thionyl chloride as an effective catalyst for thioacetalization . J. Org. Chem. 1986 , 51 , 1427 – 1431 .
  • Maatschappij , N. V. Imides. Belg. 1963 , 623 , 333 ; Chem. Abstr. 1964 , 60 , 9157d .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.