Novel Synthesis of (E)-3-Arylidene-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-ones Using Baylis-Hillman Derivatives via Reductive Cyclization

被引：9
|
作者：
Bakthadoss, Manickam [1 ]
Murugan, Gandhi [1 ]
机构：
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
来源：
SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 07期
关键词：
Baylis-Hillman reaction; benzoxazepinones; Fe; AcOH; 4-methyl; 2-nitrophenol; ADDUCTS; CONVENIENT; FRAMEWORKS;
D O I：
10.1080/00397910802519166
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple synthesis of novel (E)-3-arylidene-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-ones from bromides of the Baylis--Hillman adducts using Fe/AcOH for the in situ reduction of nitro group, into an amino group, followed by the cyclization as a key step, has been described.
引用
收藏
页码：1290 / 1298
页数：9
相关论文
共 50 条
  • [1] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF DIBENZ[B,E][1,4]OXAZEPIN-11(5H)-ONES
    RAINES, S
    KOVACS, CA
    GOLDSTEI.S
    PALOPOLI, FP
    JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (04) : 895 - &
  • [2] A Simple and Direct Synthesis of 3-Methylene-1, 4-diarylazetidin-2-ones and (E)-3-Arylidene-1-phenylazetidin-2-ones Using Baylis-Hillman Derivatives
    Bakthadoss, Manickam
    Srinivasan, Jayakumar
    Selvakumar, Raman
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2014, 67 (02) : 295 - 301
  • [3] Simple and new protocol for the synthesis of novel (z)-3-arylidenebenzothiazepin-4-ones using Baylis-Hillman derivatives
    Bakthadoss, Manickam
    Murugan, Gandhi
    SYNTHETIC COMMUNICATIONS, 2008, 38 (20) : 3406 - 3413
  • [4] Crystal structure of (Z)-3-(4-methoxy-benzylidene)-2,3-dihydrobenzo[b][1,4]-thiazepin-4(5H)-one
    Vinayagam, V.
    Raj, J. Mohan
    Murugavel, S.
    Selvakumar, R.
    Bakthadoss, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O21 - +
  • [5] Synthesis and Evaluation of Novel 2,3-Dihydrobenzo[b][1,4]dioxin- and Indolealkylamine Derivatives as Potential Antidepressants
    Wang, Songlin
    Chen, Yin
    Liu, Xinghua
    Xu, Xiangqing
    Liu, Xin
    Liu, Bi-Feng
    Zhang, Guisen
    ARCHIV DER PHARMAZIE, 2014, 347 (01) : 32 - 41
  • [6] Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3, 4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors
    Shao, Xuwei
    Pak, Steven
    Velagapudi, Uday Kiran
    Gobbooru, Shruthi
    Kommaraju, Sai Shilpa
    Low, Woon-Kai
    Subramaniam, Gopal
    Pathak, Sanjai Kumar
    Talele, Tanaji T.
    BIOORGANIC CHEMISTRY, 2020, 102
  • [7] Synthesis and crystal structure of 7-bromo-3,3-dibutyl-8-methoxy-5-phenyl-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one
    Du, Damin
    Wu, Haijian
    JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (7-8) : 437 - 440
  • [8] CYANOGEN-BROMIDE AS A REAGENT FOR LACTONE FORMATION - PREPARATION OF DIBENZ[B,E][1,4]OXAZEPIN-11-(5H)ONES
    KIM, DH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (04) : 855 - 856
  • [9] Application of primary allylamine derivatives of Baylis-Hillman adducts to heterocyclic synthesis:: Generation of 5-benzyl-4(3H)-pyrimidinones and 2-benzylidene-2,3-dihydropyrrolizin-1-ones
    Nag, Somnath
    Madapa, Sudharshan
    Batra, Sanjay
    SYNTHESIS-STUTTGART, 2008, 1 (01): : 101 - 109
  • [10] Design, synthesis and antifungal activity of (E)-3-acyl-5-(methoxyimino)-1,5-dihydrobenzo[e][1,2]oxazepin-4(3H)-one analogues
    Yang, Dongyan
    Wang, Haixia
    Fan, Zhijin
    Li, Zhengming
    Zhou, Shuang
    Hao, Zesheng
    Lv, You
    Kalinina, Tatiana A.
    Glukhareva, Tatiana V.
    MOLECULAR DIVERSITY, 2021, 25 (01) : 159 - 169
12345