An unexpected chemical behavior of 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole

被引：12
作者：
Abonia, R [1 ]
Rengifo, E
Quiroga, J
Insuasty, B
Sánchez, A
Cobo, J
Low, J
Nogueras, M
机构：
[1] Univ Valle, Dept Chem, Cali 25360, Colombia
[2] Univ Jaen, Dept Quim Inorgan & Organ, Jaen 23071, Spain
[3] Univ Aberdeen, Dept Chem, Old Aberdeen, Scotland
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期
关键词：
5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole; benzotriazole; isomerization; Troger's bases;
D O I：
10.1016/S0040-4039(02)01115-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rearrangement product or a pyrazolic Troger's base were unexpectedly obtained when 5-N-(benzotriazol-1-ylmethyl)amino-3-tert-butyl-1-phenylpyrazole was treated with electron-rich alkenes with well protic or Lewis acid catalyst, respectively, when tetrahydropyrazolopyridines were expected according with the benzotriazole methodology. The structure of the products was confirmed by NMR and X-ray diffraction techniques. Mechanisms for their formation are also proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5617 / 5620
页数：4
相关论文
共 16 条
  • [1] Synthesis of pyrazole and pyrimidine Troger's-base analogues
    Abonia, R
    Albornoz, A
    Larrahondo, H
    Quiroga, J
    Insuasty, B
    Insuasty, H
    Hormaza, A
    Sánchez, A
    Nogueras, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (13): : 1588 - 1591
  • [2] Synthesis of novel 1,2,5,6-tetrahydro-4H-pyrrolo [3,2,1-ij]-quinolines via benzotriazole methodology
    Abonia, R
    Albornoz, A
    Insuasty, B
    Quiroga, J
    Meier, H
    Hormaza, A
    Nogueras, M
    Sánchez, A
    Cobo, J
    Low, JN
    [J]. TETRAHEDRON, 2001, 57 (23) : 4933 - 4938
  • [3] CHEMISTRY OF PYRAZOLOPYRIMIDINES
    ELNAGDI, MH
    ELMOGHAYAR, MRH
    ELGEMEIE, GEH
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1987, 41 : 319 - 376
  • [4] ELNAGDI MH, 1990, ADV HETEROCYCL CHEM, V48, P223, DOI DOI 10.1016/S0065-2725(08)60340-2
  • [5] 5-[N-(1H-benzotriazol-1-ylmethyl)-amino]-3-tert-butyl-1-phenylpyrazole:: sheets built from N-H •••N, C-H •••N and C-H •••π(pyrazole) interactions
    Glidewell, C
    Low, JN
    Cobo, J
    Nogueras, M
    Sánchez, A
    Rengifo, E
    Abonia, R
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2002, 58 (06): : O314 - O317
  • [6] THE CHEMISTRY OF PYRAZOLOPYRIDINES
    HARDY, CR
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1984, 36 : 343 - 409
  • [7] INSUASTY B, 1997, TRENDS HETEROCYCLIC, V5, P83
  • [8] Katritzky AR, 1998, SYNTHESIS-STUTTGART, P1487
  • [9] REACTIONS OF N-ALKYL-N-PHENYL-1H-BENZOTRIAZOLE-1-METHANAMINES WITH N-VINYLAMIDES AND N-VINYLCARBAZOLE - A CONVENIENT SYNTHESIS OF 4-(DIALKYLAMINO)TETRAHYDROQUINOLINES
    KATRITZKY, AR
    RACHWAL, B
    RACHWAL, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) : 3993 - 4001
  • [10] The continuing magic of benzotriazole: An overview of some recent advances an synthetic methodology
    Katritzky, AR
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) : 1501 - 1522
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