Tetrazole-containing derivatives of 4-amino-3-phenylbutanoic acid

被引：6
作者：
Putis, Sergey M. [1 ]
Shuvalova, Elena S. [1 ]
Ostrovskii, Vladimir A. [1 ]
机构：
[1] St Petersburg State Inst Technol, 26 Moskowsky Av, St Petersburg 190013, Russia
来源：
ARKIVOC | 2009年
关键词：
Tetrazoles; 4-amino-3-phenylbutanoic acid; heterocyclization; esterification; acylation; SODIUM AZIDE SYSTEM; CHEMISTRY;
D O I：
10.3998/ark.5550190.0010.406
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The molecule 4-amino-3-phenylbutanoic acid contains amino and carboxy terminal groups. The reactivity of both groups was utilized for preparation of corresponding tetrazole-containing derivatives. The terminal amino group was directly replaced by a tetrazol-1-yl fragment through reaction of 4-amino-3-phenylbutanoic acid hydrochloride with triethyl orthoformate and sodium azide in acetic acid. 4-Amino-3-phenylbutanoic acid was converted into 4-(tetrazol-1-yl)-3-phenylbutanoic acid and also methyl 4-(5-methyltetrazol-1-yl)-3-phenylbutanate in 79 and 45% yields, respectively.
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收藏
页码：64 / 68
页数：5
相关论文
共 13 条
  • [1] A novel approach for the synthesis of 5-substituted tetrazole derivatives from primary amides in mild one-step method.
    ElAhl, AAS
    Elmorsy, SS
    Elbeheery, AH
    Amer, FA
    [J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1257 - 1260
  • [2] Tetrachlorosilane-sodium azide system in the synthesis of tetrazole-containing amino acid derivatives
    Esikov, KA
    Morozova, SE
    Malin, AA
    Ostrovskii, VA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (09) : 1370 - 1373
  • [3] Gaponik P.N., 1990, CHEM HETEROCYCL COMP, V26, P1274, DOI DOI 10.1007/BF00476984
  • [4] 5-substituted-1H-tetrazoles as carboxylic acid isosteres:: Medicinal chemistry and synthetic methods
    Herr, RJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) : 3379 - 3393
  • [5] Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255).: 1.: Study on structure-activity relationships and basic structure crucial for ETA antagonism
    Ishizuka, N
    Matsumura, K
    Sakai, K
    Fujimoto, M
    Mihara, S
    Yamamori, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (10) : 2041 - 2055
  • [6] Kleeman A., 2001, PHARM SUBSTANCES SYN, V2, P2488
  • [7] Mashkovskij M.D., 2007, MEDICINES, P1206
  • [8] Linear polynuclear tetrazole-containing compounds
    Morozova, SE
    Komissarov, AV
    Esikov, KA
    Zubarev, VY
    Malin, AA
    Ostrovskii, VA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (10) : 1532 - 1538
  • [9] Polynuclear tetrazole-containing amino acid analogs
    Morozova, SE
    Esikov, KA
    Zubarev, VY
    Malin, AA
    Ostrovskii, VA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (10) : 1528 - 1531
  • [10] Tetrachlorosilane-sodium azide system in the synthesis of tetrazole-containing D,L-tryptophane derivatives
    Morozova, SE
    Esikov, KA
    Dmitrieva, TN
    Malin, AA
    Ostrovskii, VA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (03) : 443 - 445
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