Araştırma Makalesi
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4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu

Yıl 2020, Cilt: 10 Sayı: 1, 368 - 377, 01.03.2020
https://doi.org/10.21597/jist.572079

Öz

4-Aminotetrahidrokinolin türevleri; organo Brønsted asit katalizörü eşliğinde anilin, N-vinilkarbamat ve substitüe halojen içeren aldehitin bir balona konulmasıyla tek kademede sentezlendi. 3 bileşenli Povarov reaksiyonu yöntemi kullanıldı. 4 farklı 4-Aminotetrahidrokinolin türevi sentezlendi ve 1H, 13C, Infrared Spektroskopisi (IR), Erime noktası (EN) ve Yüksek Çözünürlüklü Kütle Spektroskopisi (HRMS) gibi çeşitli metotlar kullanılarak yapı karakterizasyonları yapıldı.

Destekleyen Kurum

Kilis 7 Aralık Üniversitesi Yusuf Şerefoğlu Sağlık Bilimleri Fakültesi, 79000, Kilis

Teşekkür

Kilis 7 Aralık Üniversitesi İleri Teknoloji Uygulama ve Araştırma Merkezi

Kaynakça

  • Dagousset G, Zhu J, Masson G, 2011. Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Enecarbamates as Dienophiles: Highly Diastereo- and Enantioselective Synthesis of Substituted 4-Amino-tetrahydroquinolines. Journal of the American Chemical Society, 133 (37): 14804-14813.
  • Dagousset G, Drouet F, Masson G, Zhu J, 2009. Chiral Brønsted Acid-Catalyzed Enantioselective Multicomponent Mannich Reaction: Synthesis of anti-1,3-Diamines Using Enecarbamates as Nucleophiles. Organic Letters, 11 (23): 5546-5549.
  • Damon DB, Dugger RW, Hubbs SE, Scott JM, Scott RW, 2006. Asymmetric Synthesis of the Cholesteryl Ester Transfer Protein Inhibitor Torcetrapib. Organic Process Research & Development, 10, 472.
  • Dibble DJ, Umerani MJ, Mazaheripour A, Park YS, Ziller JW, Gorodetsky AA, 2015. An Aza-Diels–Alder Route to Polyquinolines. Macromolecules, 48 (3): 557-561.
  • Foster AC, Kemp JA, Leeson PD, Grimwood S, Donald AE, Marshall GI, Priestley T, Smith JD, Carling RW, 1992. Kynurenic Acid Analogues with İmproved Affinity and Selectivity for the Glycine Site on the N-Methyl-D-Aspartate Receptor from Rat Brain. Molecular Pharmacology, 41 (5): 914-922.
  • Grimwood S, Moseby AM, Carling RW, Leeson PD, Foster AC, 1992. Characterization of the Binding of [3H]L-689,560, an Antagonist for the Glycine Site on the N-methyl-D-Aspartate Receptor, to Rat Brain Membranes. Molecular Pharmacology, 41 (5): 923-930.
  • Katritzky AR, Rachwal S, Rachwal B, 1996. Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines. Tetrahedron, 52 (48): 15031-15070.
  • Kohayashi S, Ishitani H, Nagayama S, 1995. Ln(OTf)3- or Sc(OTf)3-Catalyzed Three Components Coupling Reactions between Aldehydes, Amines, and Dienes or Alkenes. Efficient Syntheses of Pyridine and Quinoline Derivatives. Chemistry Letters, 24 (6): 423-424.
  • Kouznetsov VV, Meléndez Gómez CM, Rojas Ruíz FA, del Olmo E, 2012. Simple Entry to New 2-alkyl-1,2,3,4-tetrahydroquinoline and 2,3-dialkylquinoline derivatives using BiCl3-catalyzed three Component Reactions of Anilines and Aliphatic Aldehydes in the Presence (or lack) of N-vinyl Amides. Tetrahedron Letters, 53 (25): 3115-3118.
  • Leeson PD, Carling RW, Moore KW, Moseley AM, Smith JD, Stevenson G, Chan T, Baker R, Foster AC, Grimwood S, Kemp JA, Marshall GR, Hoogsteen K, 1992. 4-Amido-2-carboxytetrahydroquinolines Structure-Activity Relationships for Antagonism at the Glycine Site of the NMDA Receptor. Journal of Medicinal Chemistry, 35 (11): 1954-1968.
  • Liu H, Dagousset G, Masson G, Retailleau P, Zhu J, 2009. Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction. Journal of the American Chemical Society, 131 (13): 4598-4599.
  • Ōmura S, Nakagawa A, 1981. Structure of Virantmycin, a Novel Antiviral Antibiotic. Tetrahedron Letters. 22 (23): 2199-2202.
  • Pearson WH, Fang WK, 2000. Synthesis of Benzo-Fused 1-Azabicyclo[m.n.0]alkanes via the Schmidt Reaction:  A Formal Synthesis of Gephyrotoxin. The Journal of Organic Chemistry, 65 (21): 7158-7174.
  • Shi F, Xing GJ, Tao ZL, Luo SW, Tu SJ, Gong LZ, 2012. An Asymmetric Organocatalytic Povarov Reaction with 2-Hydroxystyrenes. The Journal of Organic Chemistry, 77 (12): 6970-6979.
  • Shirokane K, Wada T, Yoritata M, Minamikawa R, Takayama N, Sato T, Chida N, 2014. Total Synthesis of (±)‐Gephyrotoxin by Amide‐Selective Reductive Nucleophilic Addition. Angewandte Chemie International Edition, 53 (2): 512-516.
  • Smith CD, Gavrilyuk JI, Lough AJ, Batey RA, 2010. Lewis Acid Catalyzed Three-Component Hetero-Diels−Alder (Povarov) Reaction of N-Arylimines with Strained Norbornene-Derived Dienophiles. The Journal of Organic Chemistry, 75 (3): 702-715.
  • Williamson NM, March DR, Ward AD, 1995. An İmproved Synthesis of 2,2-disubstituted-1,2-dihydroquinolines and Their Conversion to 3-chloro-2,2-disubstituted-tetrahydroquinolines Tetrahedron Letters, 36 (42): 7721-7724.
  • Witherup KM, Ransom RW, Graham AC, Bernard AM, Salvatore MJ, Lumma WC, Anderson PS, Pitzenberger SM, Varga SL, 1995. Martinelline and Martinellic Acid, Novel G-Protein Linked Receptor Antagonists from the Tropical Plant Martinella iquitosensis (Bignoniaceae) Journal of the American Chemical Society, 117 (25): 6682-6685.

Synthesis and Characterization of 4-Amino-Tetrahydroquinoline Derivatives via Organocatalyst

Yıl 2020, Cilt: 10 Sayı: 1, 368 - 377, 01.03.2020
https://doi.org/10.21597/jist.572079

Öz

4-Aminotetrahydroquinoline derivatives were synthesized as a single step by placing the aniline, N-vinylcarbamate and substituted halogen containing aldehyde in the presence of organo Brønsted acid catalyst. Three-component Povarov reaction method was used. Four different 4-aminotetrahydroquinoline derivatives were synthesized and Structural characterization was performed using various methods such as 1H, 13C, Infrared Spectroscopy (IR), melting point (MP) and High Resolution Mass Spectroscopy (HRMS).

Kaynakça

  • Dagousset G, Zhu J, Masson G, 2011. Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Enecarbamates as Dienophiles: Highly Diastereo- and Enantioselective Synthesis of Substituted 4-Amino-tetrahydroquinolines. Journal of the American Chemical Society, 133 (37): 14804-14813.
  • Dagousset G, Drouet F, Masson G, Zhu J, 2009. Chiral Brønsted Acid-Catalyzed Enantioselective Multicomponent Mannich Reaction: Synthesis of anti-1,3-Diamines Using Enecarbamates as Nucleophiles. Organic Letters, 11 (23): 5546-5549.
  • Damon DB, Dugger RW, Hubbs SE, Scott JM, Scott RW, 2006. Asymmetric Synthesis of the Cholesteryl Ester Transfer Protein Inhibitor Torcetrapib. Organic Process Research & Development, 10, 472.
  • Dibble DJ, Umerani MJ, Mazaheripour A, Park YS, Ziller JW, Gorodetsky AA, 2015. An Aza-Diels–Alder Route to Polyquinolines. Macromolecules, 48 (3): 557-561.
  • Foster AC, Kemp JA, Leeson PD, Grimwood S, Donald AE, Marshall GI, Priestley T, Smith JD, Carling RW, 1992. Kynurenic Acid Analogues with İmproved Affinity and Selectivity for the Glycine Site on the N-Methyl-D-Aspartate Receptor from Rat Brain. Molecular Pharmacology, 41 (5): 914-922.
  • Grimwood S, Moseby AM, Carling RW, Leeson PD, Foster AC, 1992. Characterization of the Binding of [3H]L-689,560, an Antagonist for the Glycine Site on the N-methyl-D-Aspartate Receptor, to Rat Brain Membranes. Molecular Pharmacology, 41 (5): 923-930.
  • Katritzky AR, Rachwal S, Rachwal B, 1996. Recent Progress in the Synthesis of 1,2,3,4-Tetrahydroquinolines. Tetrahedron, 52 (48): 15031-15070.
  • Kohayashi S, Ishitani H, Nagayama S, 1995. Ln(OTf)3- or Sc(OTf)3-Catalyzed Three Components Coupling Reactions between Aldehydes, Amines, and Dienes or Alkenes. Efficient Syntheses of Pyridine and Quinoline Derivatives. Chemistry Letters, 24 (6): 423-424.
  • Kouznetsov VV, Meléndez Gómez CM, Rojas Ruíz FA, del Olmo E, 2012. Simple Entry to New 2-alkyl-1,2,3,4-tetrahydroquinoline and 2,3-dialkylquinoline derivatives using BiCl3-catalyzed three Component Reactions of Anilines and Aliphatic Aldehydes in the Presence (or lack) of N-vinyl Amides. Tetrahedron Letters, 53 (25): 3115-3118.
  • Leeson PD, Carling RW, Moore KW, Moseley AM, Smith JD, Stevenson G, Chan T, Baker R, Foster AC, Grimwood S, Kemp JA, Marshall GR, Hoogsteen K, 1992. 4-Amido-2-carboxytetrahydroquinolines Structure-Activity Relationships for Antagonism at the Glycine Site of the NMDA Receptor. Journal of Medicinal Chemistry, 35 (11): 1954-1968.
  • Liu H, Dagousset G, Masson G, Retailleau P, Zhu J, 2009. Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction. Journal of the American Chemical Society, 131 (13): 4598-4599.
  • Ōmura S, Nakagawa A, 1981. Structure of Virantmycin, a Novel Antiviral Antibiotic. Tetrahedron Letters. 22 (23): 2199-2202.
  • Pearson WH, Fang WK, 2000. Synthesis of Benzo-Fused 1-Azabicyclo[m.n.0]alkanes via the Schmidt Reaction:  A Formal Synthesis of Gephyrotoxin. The Journal of Organic Chemistry, 65 (21): 7158-7174.
  • Shi F, Xing GJ, Tao ZL, Luo SW, Tu SJ, Gong LZ, 2012. An Asymmetric Organocatalytic Povarov Reaction with 2-Hydroxystyrenes. The Journal of Organic Chemistry, 77 (12): 6970-6979.
  • Shirokane K, Wada T, Yoritata M, Minamikawa R, Takayama N, Sato T, Chida N, 2014. Total Synthesis of (±)‐Gephyrotoxin by Amide‐Selective Reductive Nucleophilic Addition. Angewandte Chemie International Edition, 53 (2): 512-516.
  • Smith CD, Gavrilyuk JI, Lough AJ, Batey RA, 2010. Lewis Acid Catalyzed Three-Component Hetero-Diels−Alder (Povarov) Reaction of N-Arylimines with Strained Norbornene-Derived Dienophiles. The Journal of Organic Chemistry, 75 (3): 702-715.
  • Williamson NM, March DR, Ward AD, 1995. An İmproved Synthesis of 2,2-disubstituted-1,2-dihydroquinolines and Their Conversion to 3-chloro-2,2-disubstituted-tetrahydroquinolines Tetrahedron Letters, 36 (42): 7721-7724.
  • Witherup KM, Ransom RW, Graham AC, Bernard AM, Salvatore MJ, Lumma WC, Anderson PS, Pitzenberger SM, Varga SL, 1995. Martinelline and Martinellic Acid, Novel G-Protein Linked Receptor Antagonists from the Tropical Plant Martinella iquitosensis (Bignoniaceae) Journal of the American Chemical Society, 117 (25): 6682-6685.
Toplam 18 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Mustafa Zahrettin Kazancıoğlu 0000-0001-5189-2051

Yayımlanma Tarihi 1 Mart 2020
Gönderilme Tarihi 30 Mayıs 2019
Kabul Tarihi 25 Eylül 2019
Yayımlandığı Sayı Yıl 2020 Cilt: 10 Sayı: 1

Kaynak Göster

APA Zahrettin Kazancıoğlu, M. (2020). 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology, 10(1), 368-377. https://doi.org/10.21597/jist.572079
AMA Zahrettin Kazancıoğlu M. 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. Mart 2020;10(1):368-377. doi:10.21597/jist.572079
Chicago Zahrettin Kazancıoğlu, Mustafa. “4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology 10, sy. 1 (Mart 2020): 368-77. https://doi.org/10.21597/jist.572079.
EndNote Zahrettin Kazancıoğlu M (01 Mart 2020) 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology 10 1 368–377.
IEEE M. Zahrettin Kazancıoğlu, “4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu”, Iğdır Üniv. Fen Bil Enst. Der., c. 10, sy. 1, ss. 368–377, 2020, doi: 10.21597/jist.572079.
ISNAD Zahrettin Kazancıoğlu, Mustafa. “4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology 10/1 (Mart 2020), 368-377. https://doi.org/10.21597/jist.572079.
JAMA Zahrettin Kazancıoğlu M. 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2020;10:368–377.
MLA Zahrettin Kazancıoğlu, Mustafa. “4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology, c. 10, sy. 1, 2020, ss. 368-77, doi:10.21597/jist.572079.
Vancouver Zahrettin Kazancıoğlu M. 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2020;10(1):368-77.