LEWIS-ACID ASSISTED CYCLIZATION OF ARYLCYANOGUANIDINES TO 2,4-DIAMINOQUINAZOLINES

被引：7
|
作者：
JONES, ML [1 ]
KUYPER, LF [1 ]
STYLES, VL [1 ]
CADDELL, JM [1 ]
机构：
[1] BURROUGHS WELLCOME CO,CHEM DEV LABS,RES TRIANGLE PK,NC 27709
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 06期
关键词：
D O I：
10.1002/jhet.5570310668
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The mild preparation of N-cyano-N'-(1-H-indol-5-yl)guanidine and its cyclization to 1,3-diamino-7H-pyrrolo[3,2-f]quinazoline is described. Whereas previously reported methods of cyclization employed high temperatures to effect ring closure, we found that certain Lewis acids, such as boron trifluoride etherate, induce cyclization at moderate temperatures.
引用
收藏
页码：1681 / 1683
页数：3
相关论文
共 50 条
  • [21] Structure-Activity Relationship Studies of Isomeric 2,4-Diaminoquinazolines on β-Amyloid Aggregation Kinetics
    Mohamed, Tarek
    Shakeri, Arash
    Tin, Gary
    Rao, Praveen P. N.
    ACS MEDICINAL CHEMISTRY LETTERS, 2016, 7 (05): : 502 - 507
  • [22] INHIBITION OF HUMAN DIHYDROFOLATE-REDUCTASE BY 2,4-DIAMINOQUINAZOLINES BEARING SIMPLE SUBSTITUENTS ON THE AROMATIC RING
    HYNES, JB
    TOMAZIC, A
    KUMAR, A
    KUMAR, V
    FREISHEIM, JH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) : 1981 - 1986
  • [23] Potent CCR4 antagonists: Synthesis, evaluation, and docking study of 2,4-diaminoquinazolines
    Yokoyama, Kazuhiro
    Ishikawa, Noriko
    Igarashi, Susumu
    Kawano, Noriyuki
    Masuda, Naoyuki
    Hattori, Kazuyuki
    Miyazaki, Takahiro
    Ogino, Shin-ichi
    Orita, Masaya
    Matsumoto, Yuzo
    Takeuchi, Makoto
    Ohta, Mitsuaki
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) : 7968 - 7974
  • [24] SYNTHESIS AND EVALUATION OF 6-ARYLACETAMIDO-2,4-DIAMINOQUINAZOLINES AND RELATED COMPOUNDS AS FOLIC-ACID ANTAGONISTS
    HYNES, JB
    ASHTON, WT
    JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (03) : 263 - 265
  • [25] SUBSTITUTED 2,4-DIAMINOQUINAZOLINES AND 2,4-DIAMINO-8-ALKYLPURINES AS ANTAGONISTS OF THE NEUROKININ-2 (NK2) RECEPTOR
    JACOBS, RT
    MAUGER, RC
    ULATOWSKI, TG
    AHARONY, D
    BUCKNER, CK
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (23) : 2879 - 2884
  • [26] 2-(3-ACYLTHIOUREIDO)BENZONITRILES .2. SYNTHESIS OF N-SUBSTITUTED 2,4-DIAMINOQUINAZOLINES
    PAZDERA, P
    POTUCEK, V
    CHEMICAL PAPERS, 1991, 45 (05): : 677 - 686
  • [27] LEWIS-ACID PROMOTED CYCLIZATION OF ENAMIDE CONTAINING POLYENES AS A NEW ROUTE TO AZAPOLYCYCLES
    SEN, SE
    ROACH, SL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 251 - ORGN
  • [28] Discovery of potent CCR4 antagonists: Synthesis and structure-activity relationship study of 2,4-diaminoquinazolines
    Yokoyama, Kazuhiro
    Ishikawa, Noriko
    Igarashi, Susumu
    Kawano, Noriyuki
    Hattori, Kazuyuki
    Miyazaki, Takahiro
    Ogino, Shin-ichi
    Matsumoto, Yuzo
    Takeuchi, Makoto
    Ohta, Mitsuaki
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (14) : 7021 - 7032
  • [29] The effects of C5-substituted 2,4-diaminoquinazolines on selected transcript expression in spinal muscular atrophy cells
    Gentillon, Cinsley
    Connell, Andrew J.
    Kirk, Ryan W.
    Butchbach, Matthew E. R.
    PLOS ONE, 2017, 12 (06):
  • [30] REVERSIBLE INHIBITORS OF THE GASTRIC (H+/K+)-ATPASE .5. SUBSTITUTED 2,4-DIAMINOQUINAZOLINES AND THIENOPYRIMIDINES
    IFE, RJ
    BROWN, TH
    BLURTON, P
    KEELING, DJ
    LEACH, CA
    MEESON, ML
    PARSONS, ME
    THEOBALD, CJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) : 2763 - 2773
12345