4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu

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.

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

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).

Keywords:

Povarov reaction, Tetrahydroquinoline Organocatalyst,

Tam Metin

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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.

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Bibtex	`@araştırma makalesi { jist572079, journal = {Journal of the Institute of Science and Technology}, issn = {2146-0574}, eissn = {2536-4618}, address = {}, publisher = {Iğdır Üniversitesi}, year = {2020}, volume = {10}, pages = {368 - 377}, doi = {10.21597/jist.572079}, title = {4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu}, key = {cite}, author = {Zahrettin Kazancıoğlu, Mustafa} }`
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 . DOI: 10.21597/jist.572079
MLA	Zahrettin Kazancıoğlu, M . "4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu" . Journal of the Institute of Science and Technology 10 (2020 ): 368-377 <
Chicago	Zahrettin Kazancıoğlu, M . "4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu". Journal of the Institute of Science and Technology 10 (2020 ): 368-377
RIS	TY - JOUR T1 - 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu AU - Mustafa Zahrettin Kazancıoğlu Y1 - 2020 PY - 2020 N1 - doi: 10.21597/jist.572079 DO - 10.21597/jist.572079 T2 - Journal of the Institute of Science and Technology JF - Journal JO - JOR SP - 368 EP - 377 VL - 10 IS - 1 SN - 2146-0574-2536-4618 M3 - doi: 10.21597/jist.572079 UR - Y2 - 2019 ER -
EndNote	%0 Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu %A Mustafa Zahrettin Kazancıoğlu %T 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu %D 2020 %J Journal of the Institute of Science and Technology %P 2146-0574-2536-4618 %V 10 %N 1 %R doi: 10.21597/jist.572079 %U 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 .
AMA	Zahrettin Kazancıoğlu M . 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der.. 2020; 10(1): 368-377.
Vancouver	Zahrettin Kazancıoğlu M . 4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology. 2020; 10(1): 368-377.
IEEE	M. Zahrettin Kazancıoğlu , "4-Amino-Tetrahidrokinolin Türevlerinin Organokatalizör Varlığında Sentezi ve Karakterizasyonu", Journal of the Institute of Science and Technology, c. 10, sayı. 1, ss. 368-377, Mar. 2020, doi:10.21597/jist.572079