Recent advances in dibenzo[b, f][1,4]oxazepine synthesis

被引:30
|
作者
Zaware, Nilesh [1 ]
Ohlmeyer, Michael [1 ]
机构
[1] Mt Sinai Sch Med, Dept Struct & Chem Biol, New York, NY 10029 USA
关键词
copper catalysis; cyclocondensation; dibenzo[b,f][1,4]oxazepine; dibenzoxazepine; 1,3-dipolar cycloaddition; domino reaction; tricyclic; Ugi four-component reaction (U-4CR); ANALOGS; GENERATION; AGENT;
D O I
10.1515/hc-2014-0149
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dibenzo[b, f][ 1,4] oxazepine (DBO) derivatives possess an array of pharmacological activities, and are of growing pharmaceutical interest. Twelve recent synthetic protocols to construct DBO and DBO derivatives have been described in this review. The reported methods include cyclocondensation with two precursors exemplified by substituted 2-aminophenols and substituted 2-halobenzaldehydes, substituted 2-nitro-1-bromobenzene and substituted 2-triazolylphenols, substituted 2-nitro-1-bromobenzene and substituted 2-hydrazonamidophenol, substituted 2-nitro-1- bromobenzene and substituted 2-(aminomethyl) phenol, and 2- aminobenzonitrile and 1,4-dichloro-2-nitrobenzene. Other methods include copper catalysis, 1,3-dipolar cycloaddition, domino elimination-rearrangement-addition sequence, and an Ugi four-component reaction followed by an intramolecular O-arylation. These methods will serve as a guide to chemists in developing DBO derivatives of pharmacological interest.
引用
收藏
页码:251 / 256
页数:6
相关论文
共 50 条
  • [41] PREDICTION AND PREPARATION OF METABOLITES OF LOXAPINE AND AMOXAPINE (11-(4-METHYL-1-PIPERAZINYL)-2-CHLORODIBENZ[B,F] [1,4]OXAZEPINE AND 11-(1-PIPERAZINYL)-2-CHLORODIBENZ[B,F][1,4] OXAZEPINE
    HOWELL, CF
    MORTON, GO
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (MAR-A): : 25 - &
  • [42] DIBENZO[B,E][1,4]DIAZEPINES
    HANZE, AR
    STRUBE, RE
    GREIG, ME
    JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (06) : 767 - &
  • [43] DIBENZO[B,E][1,4]DIAZEPIN-1-ONES, SYNTHESIS AND DERIVATIZATION
    RASHED, N
    SAYED, M
    ELASHRY, ESH
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1993, 40 (02) : 189 - 194
  • [44] UBER IN 11-STELLUNG AMINOALKYLIERTE 5H-DIBENZO[B,E]-1,4-DIAZEPINE DIBENZO[B,F]-1,4-THIAZEPINE UND -OXAZEPINE .7. MITTEILUNG UBER SIEBENGLIEDRIGE HETEROCYCLEN
    HUNZIKER, F
    KUNZLE, F
    SCHMUTZ, J
    HELVETICA CHIMICA ACTA, 1966, 49 : 244 - &
  • [45] Na-Y Zeolite, a convenient and recyclable catalyst for the facile one-pot synthesis of spiro dibenzo[b,e][1,4]oxazepine scaffolds
    De, Kajal
    Maity, Suvendu
    Ghosh, Prasanta
    Mukhopadhyay, Chhanda
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (06)
  • [46] Iridium-catalyzed asymmetric hydrogenation of dibenzo[b,f][1,4]thiazepines
    Guo, Ran-Ning
    Gao, Kai
    Ye, Zhi-Shi
    Shi, Lei
    Li, Yanqin
    Zhou, Yong-Gui
    PURE AND APPLIED CHEMISTRY, 2013, 85 (04) : 843 - 849
  • [47] Synthesis of condensed dibenzo[b,f]pyrimido[1,6-d][1,4]oxazepines based on Biginelli products
    Baklagin, V. L.
    Bukhalin, V. V.
    Smirnova, E. A.
    Abramov, I. G.
    Filimonov, S. I.
    Ivanovsky, S. A.
    Suponitsky, K. Yu.
    RUSSIAN CHEMICAL BULLETIN, 2024, 73 (11) : 3352 - 3358
  • [48] STRUCTURE-ANALYSIS OF (+)-1,3,4,14B-TETRAHYDRO-2-METHYL-2H--DIBENZO[B,F]PYRAZINO[1,2-D][1,4]OXAZEPINE MONOHYDROBROMIDE, A POTENTIAL ANTIDEPRESSANT
    VANRIJOSKAM, JJ
    VANEGMOND, AB
    FEIL, D
    ZEELEN, FJ
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1981, 100 (11): : 433 - 434
  • [49] PREPARATION OF DIBENZ[B,F][1,4]OXAZEPINE-11-D1 AND 10,11-DIHYDRODIBENZ[B,F][1,4]OXAZEPIN-11-ONE-7-D1
    HARRISON, JM
    BREWSTER, K
    INCH, TD
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1978, 14 (03): : 369 - 373
  • [50] NEW DERIVATIVES OF DIBENZ[B,F]OXAZEPINE-1,4 WITH POTENTIAL CNS ACTIVITY
    ORZALESI, G
    SELLERI, R
    CALDINI, O
    FARMACO-EDIZIONE SCIENTIFICA, 1972, 27 (12): : 1071 - &