New Method for Preparation of 1-Amidoalkyl-2-Naphthols via Multicomponent Condensation Reaction Utilizing Tetrachlorosilane under Solvent Free Conditions
Affiliation(s)
1 Chemistry Department, Faculty of Science, Damietta University, New Damietta, Egypt. 2 Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt.
1 Chemistry Department, Faculty of Science, Damietta University, New Damietta, Egypt. 2 Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt.
ABSTRACT
An efficient and direct procedure for the synthesis of amidoalkylnaphthol derivatives employing a multi-component and one-pot condensation reaction of 2-naphthol, aromatic aldehyde and ace-tonitrile in the presence of tetrachlorosilane (TCS). A binary reagent from (TCS)/ZnCl2 was used upon applying benzonitrile.
An efficient and direct procedure for the synthesis of amidoalkylnaphthol derivatives employing a multi-component and one-pot condensation reaction of 2-naphthol, aromatic aldehyde and ace-tonitrile in the presence of tetrachlorosilane (TCS). A binary reagent from (TCS)/ZnCl2 was used upon applying benzonitrile.
Cite this paper
Said, S. , Mashaly, M. , Sheta, A. and Elmorsy, S. (2015) New Method for Preparation of 1-Amidoalkyl-2-Naphthols via Multicomponent Condensation Reaction Utilizing Tetrachlorosilane under Solvent Free Conditions. International Journal of Organic Chemistry, 5, 191-199. doi: 10.4236/ijoc.2015.53019.
Said, S. , Mashaly, M. , Sheta, A. and Elmorsy, S. (2015) New Method for Preparation of 1-Amidoalkyl-2-Naphthols via Multicomponent Condensation Reaction Utilizing Tetrachlorosilane under Solvent Free Conditions. International Journal of Organic Chemistry, 5, 191-199. doi: 10.4236/ijoc.2015.53019.
References
[1] Azumaya, I., Kagechika, H., Yamaguchi, K. and Shudo, K. (1996) Facile Formation of Aromatic Cyclic N-Methylamides Based on cis Conformational Preference. Tetrahedron Letters, 37, 5003-5006.
http://dx.doi.org/10.1016/0040-4039(96)00995-1 [2] Elmorsy, S.S., Pelter, A. and Smith, K. (1991) The Direct Production of Tri- and Hexa-Substituted Benzenes from Ketones Under Mild Conditions. Tetrahedron Letters, 32, 4175-4176.
http://dx.doi.org/10.1016/S0040-4039(00)79896-0 [3] Elmorsy, S.S., Pelter, A., Smith, K., Hursthouse, M.B. and Ando, D. (1992) Investigations of the Tetrachlorosilane-Ethanol Induced Self Condensations of Ketones. Tetrahedron Letters, 33, 821-824.
http://dx.doi.org/10.1016/S0040-4039(00)77724-0 [4] Elmorsy, S.S., Khalil, A.M., Girges, M.M. and Salama, T.A. (1997) A New Approach to the Stereoselective Synthesis of β-Methylchalcones. Journal of Chemical Research, Synopses, No. 7, 232-233.
http://dx.doi.org/10.1039/a607611d [5] Elmorsy, S.S., El-Ahl, A.S., Soliman, H.A. and Amer, F.A. (1995) Synthesis of Triazidochlorosilane (TACS). A Novel Silicon Mediated One Pot Conversion of Aldehydes to Nitriles. Tetrahedron Letters, 36, 2639-2640.
http://dx.doi.org/10.1016/0040-4039(95)00302-S [6] Salama, T.A., El-Ahl, A.S., Khalil, A.M., Girges, M.M., Lackner, B., Steindi, C. and Elmorsy, S.S. (2003) A Convenient Regiospecific Synthesis of New Conjugated Tetrazole Derivatives via the Reaction of Dienones with the Tetrachlorosilane-Sodium Azide Reagent and their NMR Structural Assignment. Monatshefte für Chemie, 134, 1241-1252. http://dx.doi.org/10.1007/s00706-003-0045-x [7] Salama, T.A., Elmorsy, S.S., Khalil, A. M., Girges, M.M. and El-Ahl, A.S. (2007) Novel Uncatalyzed Hydrocyanation of Ketones utlizing Tetrachlorosilane-Potassium Cyanide Reagent. Synthetic Communications, 37, 1313-1319.
http://dx.doi.org/10.1080/00397910701226897 [8] Salama, T.A., Elmorsy, S.S., Khalil, A.M. and Ismail, M.A. (2007) A SiCl4-ZnCl2 Induced General, Mild and Efficient One-Pot, Three-Component Synthesis of β-Amido Ketone Libraries. Tetrahedron Letters, 48, 6199-6203.
http://dx.doi.org/10.1016/j.tetlet.2007.06.128 [9] Salama, A.T., Ismail, A.M., Khalil, M.A. and Elmorsy, S.S. (2012) Silicon-Assisted O-Heterocyclic Synthesis: Mild and Efficient One-Pot Syntheses of (E)-3-Benzylideneflavanones, Coumarin-3-Carbonitriles/Carboxamides, and Benzannulated Spiropyran Derivatives. Archive for Organic Chemistry, 2012, 242-253. [10] Thomson, L.A. and Elman, J.A. (1996) Synthesis and Applications of Small Molecule Libraries. Chemical Reviews, 96, 555-600.
http://dx.doi.org/10.1021/cr9402081 [11] Hulme, C. and Gore, V. (2003) Multi-Component Reactions: Emerging Chemistry in Drug Discovery “From Xylocain to Crixivan”. Current Medicinal Chemistry, 10, 51-80.
http://dx.doi.org/10.2174/0929867033368600 [12] Selvam, N.P. and Perumal, P.T. (2006) A New Synthesis of Acet-amido Phenols Promoted by Ce(SO4)2. Tetrahedron Letters, 47, 7481-7483.
http://dx.doi.org/10.1016/j.tetlet.2006.08.038 [13] Kantevari, S., Vuppalapati, S.V.N. and Nagarapu, L. (2007) Mont-morillonite K10 Catalyzed Efficient Synthesis of Amidoalkyl Naphthols under Solvent Free Conditions. Catalysis Commu-nications, 8, 1857-1862.
http://dx.doi.org/10.1016/j.catcom.2007.02.022 [14] Das, B., Laxminarayana, K., Ravikanth, B. and Rao, B.R. (2007) Iodine Catalyzed Preparation of Amidoalkyl Naphthols in Solution and under Solvent-Free Conditions. Journal of Molecular Catalysis A: Chemical, 261, 180-183.
http://dx.doi.org/10.1016/j.molcata.2006.07.077 [15] Patil, S.B., Singh, P.R., Surpur, M.P. and Samant, S.D. (2007) Cation-Exchanged Resins: Efficient Heterogeneous Catalysts for Facile Synthesis of 1-Amidoalkyl-2-naphthols from One-Pot, Three-Component Condensations of Amides/Ureas, Aldehydes, and 2-Naphthol. Synthetic Communications, 37, 1659-1664.
http://dx.doi.org/10.1080/00397910701263858 [16] Shaterian, H.R. and Yarahmadi, H. (2008) Sodium Hydrogen Sulfate as Effective and Reusable Heterogeneous Catalyst for the One-Pot Preparation of Amidoalkyl Naphthols. ARKIVOC, 2008, 105-114.
http://www.arkat-usa.org/get-file/23225/ [17] Shaterian, H.R., Yarahmadi, H. and Ghashang, M. (2008) An Efficient, Simple and Expedition Synthesis of 1-Amidoalkyl-2-naphthols as “Drug Like” Molecules for Biological Screening. Bioorganic & Medicinal Chemistry Letters, 18, 788-792.
http://dx.doi.org/10.1016/j.bmcl.2007.11.035 [18] Patil, S.B., Singh, P.R., Surpur, M.P. and Samant, S.D. (2007) Ultrasound-Promoted Synthesis of 1-Amidoalkyl-2- naphthols via a Three-Component Condensation of 2-Naphthol, Ureas/Amides, and Aldehydes, Catalyzed by Sulfamic Acid under Ambient Conditions. Ultrasonics Sonochemistry, 14, 515-518.
http://dx.doi.org/10.1016/j.ultsonch.2006.09.006 [19] Shaterian, H.R., Yarahmadi, H. and Ghashang, M. (2008) Silica Supported Perchloric Acid (HClO4-SiO2): An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of Amidoalkyl Naphthols. Tetrahedron, 64, 1263-1269.
http://dx.doi.org/10.1016/j.tet.2007.11.070 [20] Mahdavinia, G.H. and Bigdeli, M.A. (2009) Wet Cyanuric Chloride Promoted Efficient Synthesis of Amidoalkyl Naphthols under Solvent-Free Conditions. Chinese Chemical Letters, 20, 383-386.
http://dx.doi.org/10.1016/j.cclet.2008.12.018 [21] Nagarapu, L., Baseeruddin, M., Apuri, S. and Kantevari, S. (2007) Potassium Dodecatungstocobaltate Trihydrate (K5CoW12O40?3H2O): A Mild and Efficient Reusable Catalyst for the Synthesis of Amidoalkyl Naphthols in Solution and under Solvent-Free Conditions. Catalysis Communications, 8, 1729-1734.
http://dx.doi.org/10.1016/j.catcom.2007.02.008 [22] Zare, A., Hasaninejad, A., Rostami, E., Moosavi-Zare, A.R., Roshankar, N., Khedri, F. and Khedri, M. (2010) An Efficient Solvent-Free Protocol for the Synthesis of 1-Amidoalkyl-2-naphthols Using Silica-Supported Molybdatophosphoric Acid. E-Journal of Chemistry, 7, 1162-1169.
http://dx.doi.org/10.1155/2010/512392 [23] Zandi, M. and Sardarian, A.R. (2012) Eco-Friendly and Efficient Multi-Component Method for Preparation of 1- Amidoalkyl-2-naphthols under Solvent-Free Conditions by Dodecylphosphonic Acid (DPA). Comptes Rendus Chimie, 15, 365-369.
http://dx.doi.org/10.1016/j.crci.2011.11.012 [24] Shahrisa, A., Somayehesmati and Nazari, M.G. (2012) Boric Acid as a Mild and Efficient Catalyst for One-Pot Synthesis of 1-Amidoalkyl-2-naphthols under Solvent-Free Conditions. Journal of Chemical Sciences, 124, 927-931.
http://dx.doi.org/10.1007/s12039-012-0285-6 [25] Nandi, G.C, Samai, S., Kumar, R. and Singh, M.S (2009) Atom-Efficient and Environment-Friendly Multicomponent Synthesis of Amidoalkyl Naphthols Catalyzed by P2O5. Tetra-hedron Letters, 50, 7220-7222.
http://dx.doi.org/10.1016/j.tetlet.2009.10.055 [26] Nagawade, R.R. and Shinde, D.B. (2007) Zirconyl(IV) Chloride—Catalyzed Multicomponent Reaction of β-Naphthols: An Expeditious Synthesis of Amidoalkyl Naphthols. Acta Chimica Slovenica, 54, 642-646. [27] Sapanamalik, S. and Singh, R.K. (2012) Microwave Assisted Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Anhydrous Zinc Chloride. Asian Journal of Chemistry, 24, 5669-5672. [28] Jiang, W.Q.L., An, T.J. and Zou, P. (2008) Molybdophosphoric Acid: An Efficient Keggin-Type Hetero-poloacid Catalyst for the One-Pot Three-Component Synthesis of 1-Amidoalkyl-2-naphthols. Chinese Journal of Chemistry, 26, 1697-1701.
http://dx.doi.org/10.1002/cjoc.200890307 [29] Dingermann, T., Steinhilber, D. and Folkers, G. (2004) Molecular Biology in Medicinal Chemistry. Wiley-VCH, Weinheim. [30] Shen, A.Y., Tsai, C.T. and Chen, C.L. (1999) Synthesis and Cardiovascular Evaluation of N-Substituted 1-Aminomethyl-2-naphthols. European Journal of Medicinal Chemistry, 34, 877-882.
http://dx.doi.org/10.1016/S0223-5234(99)00204-4 [31] Shen, A.Y., Chen, C.L. and Lin, C.I. (1992) Electrophysiological Basis for the Bradycardic Effects of 1-(1-Pyrrolidi-nylmethyl)-2-naphthol in Rodents. Chinese Journal of Physiology, 35, 45-54. [32] Khodaei, M.M., Khosropour, A.R. and Oghanian, H.M. (2006) A Simple and Efficient Procedure for the Synthesis of Amidoalkyl Naphthols by p-TSA in Solution or under Solvent-Free Conditions. Synlett, 2006, 916-920.
http://dx.doi.org/10.1055/s-2006-939034 [33] Haaf, W. (1963) Studies on Ritter Reaction. Chemische Berichte, 96, 3359-3369.
http://dx.doi.org/10.1002/cber.19630961237 [34] Ziegler, E., Kleineberg, G. and Meindle, H. (1963) Synthesen von Heterocyclen, 46. Mitt.: über Reaktionen mit Ketens?urechloriden (Kurze vorl?ufige Mitteilung). Monatshefte für Chemie, 94, 544-548.
http://dx.doi.org/10.1007/BF00903495 [35] Ritter, J.J. and Minieri, P.P. (1948) A New Reaction of Nitriles. I. Amides from Alkenes and Mononitriles. Journal of the American Chemical Society, 70, 4045-4048.
http://dx.doi.org/10.1021/ja01192a022 [36] Tillmanns, E.J. and Ritter, J.J. (1957) Notes-Nitriles in Nuclear Heterocyclic Syntheses. I. Dihydro-1,3 Oxazines. The Journal of Organic Chemistry, 22, 839-840.
http://dx.doi.org/10.1021/jo01358a612 [37] Smith, P.A.S. and Sullivan, J.M. (1961) The Cyclization of N-Alkenylthionamides to Thiazolines and Dihydrothiazines. The Journal of Organic Chemistry, 26, 1132-1136.
http://dx.doi.org/10.1021/jo01063a038
[1] Azumaya, I., Kagechika, H., Yamaguchi, K. and Shudo, K. (1996) Facile Formation of Aromatic Cyclic N-Methylamides Based on cis Conformational Preference. Tetrahedron Letters, 37, 5003-5006.
http://dx.doi.org/10.1016/0040-4039(96)00995-1 [2] Elmorsy, S.S., Pelter, A. and Smith, K. (1991) The Direct Production of Tri- and Hexa-Substituted Benzenes from Ketones Under Mild Conditions. Tetrahedron Letters, 32, 4175-4176.
http://dx.doi.org/10.1016/S0040-4039(00)79896-0 [3] Elmorsy, S.S., Pelter, A., Smith, K., Hursthouse, M.B. and Ando, D. (1992) Investigations of the Tetrachlorosilane-Ethanol Induced Self Condensations of Ketones. Tetrahedron Letters, 33, 821-824.
http://dx.doi.org/10.1016/S0040-4039(00)77724-0 [4] Elmorsy, S.S., Khalil, A.M., Girges, M.M. and Salama, T.A. (1997) A New Approach to the Stereoselective Synthesis of β-Methylchalcones. Journal of Chemical Research, Synopses, No. 7, 232-233.
http://dx.doi.org/10.1039/a607611d [5] Elmorsy, S.S., El-Ahl, A.S., Soliman, H.A. and Amer, F.A. (1995) Synthesis of Triazidochlorosilane (TACS). A Novel Silicon Mediated One Pot Conversion of Aldehydes to Nitriles. Tetrahedron Letters, 36, 2639-2640.
http://dx.doi.org/10.1016/0040-4039(95)00302-S [6] Salama, T.A., El-Ahl, A.S., Khalil, A.M., Girges, M.M., Lackner, B., Steindi, C. and Elmorsy, S.S. (2003) A Convenient Regiospecific Synthesis of New Conjugated Tetrazole Derivatives via the Reaction of Dienones with the Tetrachlorosilane-Sodium Azide Reagent and their NMR Structural Assignment. Monatshefte für Chemie, 134, 1241-1252. http://dx.doi.org/10.1007/s00706-003-0045-x [7] Salama, T.A., Elmorsy, S.S., Khalil, A. M., Girges, M.M. and El-Ahl, A.S. (2007) Novel Uncatalyzed Hydrocyanation of Ketones utlizing Tetrachlorosilane-Potassium Cyanide Reagent. Synthetic Communications, 37, 1313-1319.
http://dx.doi.org/10.1080/00397910701226897 [8] Salama, T.A., Elmorsy, S.S., Khalil, A.M. and Ismail, M.A. (2007) A SiCl4-ZnCl2 Induced General, Mild and Efficient One-Pot, Three-Component Synthesis of β-Amido Ketone Libraries. Tetrahedron Letters, 48, 6199-6203.
http://dx.doi.org/10.1016/j.tetlet.2007.06.128 [9] Salama, A.T., Ismail, A.M., Khalil, M.A. and Elmorsy, S.S. (2012) Silicon-Assisted O-Heterocyclic Synthesis: Mild and Efficient One-Pot Syntheses of (E)-3-Benzylideneflavanones, Coumarin-3-Carbonitriles/Carboxamides, and Benzannulated Spiropyran Derivatives. Archive for Organic Chemistry, 2012, 242-253. [10] Thomson, L.A. and Elman, J.A. (1996) Synthesis and Applications of Small Molecule Libraries. Chemical Reviews, 96, 555-600.
http://dx.doi.org/10.1021/cr9402081 [11] Hulme, C. and Gore, V. (2003) Multi-Component Reactions: Emerging Chemistry in Drug Discovery “From Xylocain to Crixivan”. Current Medicinal Chemistry, 10, 51-80.
http://dx.doi.org/10.2174/0929867033368600 [12] Selvam, N.P. and Perumal, P.T. (2006) A New Synthesis of Acet-amido Phenols Promoted by Ce(SO4)2. Tetrahedron Letters, 47, 7481-7483.
http://dx.doi.org/10.1016/j.tetlet.2006.08.038 [13] Kantevari, S., Vuppalapati, S.V.N. and Nagarapu, L. (2007) Mont-morillonite K10 Catalyzed Efficient Synthesis of Amidoalkyl Naphthols under Solvent Free Conditions. Catalysis Commu-nications, 8, 1857-1862.
http://dx.doi.org/10.1016/j.catcom.2007.02.022 [14] Das, B., Laxminarayana, K., Ravikanth, B. and Rao, B.R. (2007) Iodine Catalyzed Preparation of Amidoalkyl Naphthols in Solution and under Solvent-Free Conditions. Journal of Molecular Catalysis A: Chemical, 261, 180-183.
http://dx.doi.org/10.1016/j.molcata.2006.07.077 [15] Patil, S.B., Singh, P.R., Surpur, M.P. and Samant, S.D. (2007) Cation-Exchanged Resins: Efficient Heterogeneous Catalysts for Facile Synthesis of 1-Amidoalkyl-2-naphthols from One-Pot, Three-Component Condensations of Amides/Ureas, Aldehydes, and 2-Naphthol. Synthetic Communications, 37, 1659-1664.
http://dx.doi.org/10.1080/00397910701263858 [16] Shaterian, H.R. and Yarahmadi, H. (2008) Sodium Hydrogen Sulfate as Effective and Reusable Heterogeneous Catalyst for the One-Pot Preparation of Amidoalkyl Naphthols. ARKIVOC, 2008, 105-114.
http://www.arkat-usa.org/get-file/23225/ [17] Shaterian, H.R., Yarahmadi, H. and Ghashang, M. (2008) An Efficient, Simple and Expedition Synthesis of 1-Amidoalkyl-2-naphthols as “Drug Like” Molecules for Biological Screening. Bioorganic & Medicinal Chemistry Letters, 18, 788-792.
http://dx.doi.org/10.1016/j.bmcl.2007.11.035 [18] Patil, S.B., Singh, P.R., Surpur, M.P. and Samant, S.D. (2007) Ultrasound-Promoted Synthesis of 1-Amidoalkyl-2- naphthols via a Three-Component Condensation of 2-Naphthol, Ureas/Amides, and Aldehydes, Catalyzed by Sulfamic Acid under Ambient Conditions. Ultrasonics Sonochemistry, 14, 515-518.
http://dx.doi.org/10.1016/j.ultsonch.2006.09.006 [19] Shaterian, H.R., Yarahmadi, H. and Ghashang, M. (2008) Silica Supported Perchloric Acid (HClO4-SiO2): An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of Amidoalkyl Naphthols. Tetrahedron, 64, 1263-1269.
http://dx.doi.org/10.1016/j.tet.2007.11.070 [20] Mahdavinia, G.H. and Bigdeli, M.A. (2009) Wet Cyanuric Chloride Promoted Efficient Synthesis of Amidoalkyl Naphthols under Solvent-Free Conditions. Chinese Chemical Letters, 20, 383-386.
http://dx.doi.org/10.1016/j.cclet.2008.12.018 [21] Nagarapu, L., Baseeruddin, M., Apuri, S. and Kantevari, S. (2007) Potassium Dodecatungstocobaltate Trihydrate (K5CoW12O40?3H2O): A Mild and Efficient Reusable Catalyst for the Synthesis of Amidoalkyl Naphthols in Solution and under Solvent-Free Conditions. Catalysis Communications, 8, 1729-1734.
http://dx.doi.org/10.1016/j.catcom.2007.02.008 [22] Zare, A., Hasaninejad, A., Rostami, E., Moosavi-Zare, A.R., Roshankar, N., Khedri, F. and Khedri, M. (2010) An Efficient Solvent-Free Protocol for the Synthesis of 1-Amidoalkyl-2-naphthols Using Silica-Supported Molybdatophosphoric Acid. E-Journal of Chemistry, 7, 1162-1169.
http://dx.doi.org/10.1155/2010/512392 [23] Zandi, M. and Sardarian, A.R. (2012) Eco-Friendly and Efficient Multi-Component Method for Preparation of 1- Amidoalkyl-2-naphthols under Solvent-Free Conditions by Dodecylphosphonic Acid (DPA). Comptes Rendus Chimie, 15, 365-369.
http://dx.doi.org/10.1016/j.crci.2011.11.012 [24] Shahrisa, A., Somayehesmati and Nazari, M.G. (2012) Boric Acid as a Mild and Efficient Catalyst for One-Pot Synthesis of 1-Amidoalkyl-2-naphthols under Solvent-Free Conditions. Journal of Chemical Sciences, 124, 927-931.
http://dx.doi.org/10.1007/s12039-012-0285-6 [25] Nandi, G.C, Samai, S., Kumar, R. and Singh, M.S (2009) Atom-Efficient and Environment-Friendly Multicomponent Synthesis of Amidoalkyl Naphthols Catalyzed by P2O5. Tetra-hedron Letters, 50, 7220-7222.
http://dx.doi.org/10.1016/j.tetlet.2009.10.055 [26] Nagawade, R.R. and Shinde, D.B. (2007) Zirconyl(IV) Chloride—Catalyzed Multicomponent Reaction of β-Naphthols: An Expeditious Synthesis of Amidoalkyl Naphthols. Acta Chimica Slovenica, 54, 642-646. [27] Sapanamalik, S. and Singh, R.K. (2012) Microwave Assisted Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Anhydrous Zinc Chloride. Asian Journal of Chemistry, 24, 5669-5672. [28] Jiang, W.Q.L., An, T.J. and Zou, P. (2008) Molybdophosphoric Acid: An Efficient Keggin-Type Hetero-poloacid Catalyst for the One-Pot Three-Component Synthesis of 1-Amidoalkyl-2-naphthols. Chinese Journal of Chemistry, 26, 1697-1701.
http://dx.doi.org/10.1002/cjoc.200890307 [29] Dingermann, T., Steinhilber, D. and Folkers, G. (2004) Molecular Biology in Medicinal Chemistry. Wiley-VCH, Weinheim. [30] Shen, A.Y., Tsai, C.T. and Chen, C.L. (1999) Synthesis and Cardiovascular Evaluation of N-Substituted 1-Aminomethyl-2-naphthols. European Journal of Medicinal Chemistry, 34, 877-882.
http://dx.doi.org/10.1016/S0223-5234(99)00204-4 [31] Shen, A.Y., Chen, C.L. and Lin, C.I. (1992) Electrophysiological Basis for the Bradycardic Effects of 1-(1-Pyrrolidi-nylmethyl)-2-naphthol in Rodents. Chinese Journal of Physiology, 35, 45-54. [32] Khodaei, M.M., Khosropour, A.R. and Oghanian, H.M. (2006) A Simple and Efficient Procedure for the Synthesis of Amidoalkyl Naphthols by p-TSA in Solution or under Solvent-Free Conditions. Synlett, 2006, 916-920.
http://dx.doi.org/10.1055/s-2006-939034 [33] Haaf, W. (1963) Studies on Ritter Reaction. Chemische Berichte, 96, 3359-3369.
http://dx.doi.org/10.1002/cber.19630961237 [34] Ziegler, E., Kleineberg, G. and Meindle, H. (1963) Synthesen von Heterocyclen, 46. Mitt.: über Reaktionen mit Ketens?urechloriden (Kurze vorl?ufige Mitteilung). Monatshefte für Chemie, 94, 544-548.
http://dx.doi.org/10.1007/BF00903495 [35] Ritter, J.J. and Minieri, P.P. (1948) A New Reaction of Nitriles. I. Amides from Alkenes and Mononitriles. Journal of the American Chemical Society, 70, 4045-4048.
http://dx.doi.org/10.1021/ja01192a022 [36] Tillmanns, E.J. and Ritter, J.J. (1957) Notes-Nitriles in Nuclear Heterocyclic Syntheses. I. Dihydro-1,3 Oxazines. The Journal of Organic Chemistry, 22, 839-840.
http://dx.doi.org/10.1021/jo01358a612 [37] Smith, P.A.S. and Sullivan, J.M. (1961) The Cyclization of N-Alkenylthionamides to Thiazolines and Dihydrothiazines. The Journal of Organic Chemistry, 26, 1132-1136.
http://dx.doi.org/10.1021/jo01063a038