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Year 2014, Volume: 4 Issue: 2, 26 - 30, 27.02.2015
https://doi.org/10.17678/beujst.39968

Abstract

References

  • Arisawa M, Theeraladanon C, Nishida A (2005). Preparation of N-sulfonyl-quinoline using ring-closing metathesis (RCM). Heterocycles 66, 683.
  • Belley M, Chan CC, Gareau Y, Gallant M, Juteau H, Houde, K, Lachance N, Labelle M, Sawyer N, Tremblay N, Lamontagne S, Carriere, MC, Denis D, Greig G, Slipetz D, Gordon R, Chauret N, Li C, Zamboni R J, Metters, K (2006). Comparison between two classes of selective EP(3) antagonists and their biological activities. Bioorg Med Chem Lett 16, 5639.
  • Cheeseman GWH, Varvounis GJ (1988). Synthesis of some Pyrrolobenzothiadiazocines. Heterocycl. Chem 25, 431.
  • CS ChemBioDraw Ultra 12.0 Download Individual One Year Term English Windows, 2010.
  • Chiacchio U, Corsaro A, Gambera G, Rescifina A, Piperno, A, Romeo R, Romeo G (2002). Syntheses of new chiral bicyclic sultams and their use as auxiliaries in asymmetric conjugate addition of Grignard reagents. Tetrahedron: Asymmetry 13, 1915-1921.
  • Foresman JB, Frisch AE (1996). Exploring Chemistry with Electronic Structure Methods. 2ed Gaussian Inc.
  • Frisch AE et al., Gaussian 09W Revision A.02, Gaussian Inc, Wallingford CT, 2009.
  • Gaussian 09. Revision B.01. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramill J, Gomperts R, Stratmann RE, YazyevO, Austin AJ, R. Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ, Gaussian Inc.. Wallingford CT 2009.
  • Hajra S, Maji B, Karmakar A (2005). Lewis Acid Catalyzed Intramolecular Halo-Arylation of Tethered alkenes using NXS as a Halonium Source: A General Method for the Synthesis of Chromanons, Chromans, Quinolones, Tetrahydroquinolines and Tetralins. Tetrahedron Lett 46, 8599.
  • Hayashi T, Kawai M, Tokunaga N (2004). Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines. Angew Chem Int Ed 43, 6125.
  • Heyboer J, Staverman AJ (1950). Some derivatives of methacrylic acid. Recl Trav Chim Pays-Bas 69, 787.
  • Homsi F, Rousseau G J (1999). 4-Endo-Trig Cyclization Processes Using Bis(collidine)bromine(I) Hexafluorophosphate as Reagent: Preparation of 2-Oxetanones, 2-Azetidinones, and Oxetanes. Org Chem 64, 81-85.
  • Itsuki Y, Shibata T, Kajiki R, Kose K, Yamaji K, Takahashi S (2005). Jpn. Kokai Tokkya Koho, 39.
  • Juteau H, Gareau Y, Labelle M, Sturino CF, Sawyer N, Tremblay N, Lamontagne S, Carriere MC, Denis D, Metters, KM (2001). Structure-activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor. Bioorg Med Chem 9, 1977.
  • Katritzky AR, Hanci S, Meher NK (2009) Preparation of N-(α,β-unsaturated acyl)-sulfonamides. Arkivoc (iv), 115-124.
  • Katritzky AR, Meher NK, Singh SK (2005). Gamma,delta-unsaturated beta-diketones by acylation of ketones. J Org Chem 70, 7792.
  • Knowles HS, Parsons AF, Pettifer RM, Rickling S (2000). Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods. Tetrahedron 56, 979.
  • Lyutenko NV, Gerus II, Kacharov AD, Kukhar V (2003). Regioselective reactions of β-aminovinyl trifluoromethyl ketones with tosyl isocyanate. P Tetrahedron 59, 1731-1738.
  • Marvin Beans, MarvinView 14.7.7 program downloaded individually from website chemaxon.com agreement with Terms of service 2014.
  • Nagashima H, Ozaki N, Washiyama M, Itoh K (1985). Conjugate addition of organocopper reagents to n-tosylated α, β- unsaturated amides. Tetrahedron Lett 26, 657-660.
  • Niestroj M, Neumann, WP, Thies O (1994). Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates) Chem Ber 127, 1131-1136.
  • Oppolzer W, Kingma A. J, Poli, G (1989). Asymmetric 1,4-additions of Gilman reagents to α,β-disubstituted (e)-enoylsultams/“enolate”protonations. Tetrahedron 45, 479-488.
  • Reddy CR, Mahipal B, Yaragorla SR (2007). A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis. Tetrahedron Lett 48, 7528-7532.
  • Xu W, Kong A, Lu XJ (2006). Palladium(II)-Catalyzed Asymmetric Synthesis of (Z)-a-Alkylidene-g-Butyrolactams from (Z)-N-Allylic 2- Alkynamides. Total Synthesis of (-)-Isocynometrine. Org Chem 71, 3854-3858.

Theoretical calculations of some new N-(α,β-Unsaturated acyl)sulfonamides and an investigation on correlations with those experimental values

Year 2014, Volume: 4 Issue: 2, 26 - 30, 27.02.2015
https://doi.org/10.17678/beujst.39968

Abstract

Previously some new N-(α,β-Unsaturated acyl)sulfonamides are prepared (i) by the N-acylation of sulfonamides with N-(α,β-unsaturated acyl)benzotriazoles in the presence of potassium tert-butoxide and (ii) by reactions of appropriate α,β-unsaturated carboxamides with sulfonylbenzotriazoles in the presence of sodium hydride. The reaction efficiency has been changed related to route i or ii. Certain theoretical properties of N-(α,β-Unsaturated acyl)sulfonamides and reactants were calculated in Gaussian09 program using DFT method at B3LYP/6-311+g(d,p) level of theory. The theoretical data was then compared with certain experimental results.

References

  • Arisawa M, Theeraladanon C, Nishida A (2005). Preparation of N-sulfonyl-quinoline using ring-closing metathesis (RCM). Heterocycles 66, 683.
  • Belley M, Chan CC, Gareau Y, Gallant M, Juteau H, Houde, K, Lachance N, Labelle M, Sawyer N, Tremblay N, Lamontagne S, Carriere, MC, Denis D, Greig G, Slipetz D, Gordon R, Chauret N, Li C, Zamboni R J, Metters, K (2006). Comparison between two classes of selective EP(3) antagonists and their biological activities. Bioorg Med Chem Lett 16, 5639.
  • Cheeseman GWH, Varvounis GJ (1988). Synthesis of some Pyrrolobenzothiadiazocines. Heterocycl. Chem 25, 431.
  • CS ChemBioDraw Ultra 12.0 Download Individual One Year Term English Windows, 2010.
  • Chiacchio U, Corsaro A, Gambera G, Rescifina A, Piperno, A, Romeo R, Romeo G (2002). Syntheses of new chiral bicyclic sultams and their use as auxiliaries in asymmetric conjugate addition of Grignard reagents. Tetrahedron: Asymmetry 13, 1915-1921.
  • Foresman JB, Frisch AE (1996). Exploring Chemistry with Electronic Structure Methods. 2ed Gaussian Inc.
  • Frisch AE et al., Gaussian 09W Revision A.02, Gaussian Inc, Wallingford CT, 2009.
  • Gaussian 09. Revision B.01. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramill J, Gomperts R, Stratmann RE, YazyevO, Austin AJ, R. Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ, Gaussian Inc.. Wallingford CT 2009.
  • Hajra S, Maji B, Karmakar A (2005). Lewis Acid Catalyzed Intramolecular Halo-Arylation of Tethered alkenes using NXS as a Halonium Source: A General Method for the Synthesis of Chromanons, Chromans, Quinolones, Tetrahydroquinolines and Tetralins. Tetrahedron Lett 46, 8599.
  • Hayashi T, Kawai M, Tokunaga N (2004). Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines. Angew Chem Int Ed 43, 6125.
  • Heyboer J, Staverman AJ (1950). Some derivatives of methacrylic acid. Recl Trav Chim Pays-Bas 69, 787.
  • Homsi F, Rousseau G J (1999). 4-Endo-Trig Cyclization Processes Using Bis(collidine)bromine(I) Hexafluorophosphate as Reagent: Preparation of 2-Oxetanones, 2-Azetidinones, and Oxetanes. Org Chem 64, 81-85.
  • Itsuki Y, Shibata T, Kajiki R, Kose K, Yamaji K, Takahashi S (2005). Jpn. Kokai Tokkya Koho, 39.
  • Juteau H, Gareau Y, Labelle M, Sturino CF, Sawyer N, Tremblay N, Lamontagne S, Carriere MC, Denis D, Metters, KM (2001). Structure-activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor. Bioorg Med Chem 9, 1977.
  • Katritzky AR, Hanci S, Meher NK (2009) Preparation of N-(α,β-unsaturated acyl)-sulfonamides. Arkivoc (iv), 115-124.
  • Katritzky AR, Meher NK, Singh SK (2005). Gamma,delta-unsaturated beta-diketones by acylation of ketones. J Org Chem 70, 7792.
  • Knowles HS, Parsons AF, Pettifer RM, Rickling S (2000). Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods. Tetrahedron 56, 979.
  • Lyutenko NV, Gerus II, Kacharov AD, Kukhar V (2003). Regioselective reactions of β-aminovinyl trifluoromethyl ketones with tosyl isocyanate. P Tetrahedron 59, 1731-1738.
  • Marvin Beans, MarvinView 14.7.7 program downloaded individually from website chemaxon.com agreement with Terms of service 2014.
  • Nagashima H, Ozaki N, Washiyama M, Itoh K (1985). Conjugate addition of organocopper reagents to n-tosylated α, β- unsaturated amides. Tetrahedron Lett 26, 657-660.
  • Niestroj M, Neumann, WP, Thies O (1994). Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates) Chem Ber 127, 1131-1136.
  • Oppolzer W, Kingma A. J, Poli, G (1989). Asymmetric 1,4-additions of Gilman reagents to α,β-disubstituted (e)-enoylsultams/“enolate”protonations. Tetrahedron 45, 479-488.
  • Reddy CR, Mahipal B, Yaragorla SR (2007). A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis. Tetrahedron Lett 48, 7528-7532.
  • Xu W, Kong A, Lu XJ (2006). Palladium(II)-Catalyzed Asymmetric Synthesis of (Z)-a-Alkylidene-g-Butyrolactams from (Z)-N-Allylic 2- Alkynamides. Total Synthesis of (-)-Isocynometrine. Org Chem 71, 3854-3858.
There are 24 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Süreyya Musalli This is me

Publication Date February 27, 2015
Submission Date October 19, 2014
Published in Issue Year 2014 Volume: 4 Issue: 2

Cite

IEEE S. Musalli, “Theoretical calculations of some new N-(α,β-Unsaturated acyl)sulfonamides and an investigation on correlations with those experimental values”, Bitlis Eren University Journal of Science and Technology, vol. 4, no. 2, pp. 26–30, 2015, doi: 10.17678/beujst.39968.