One Pot Regioselective Synthesis of a Small Library of Dibenzo[b,f][1,4]thiazepin-11(10H)-ones via Smiles Rearrangement

被引:14
作者
Zhao, Yongmei [1 ]
Dai, Qiaoling [1 ]
Chen, Zhi [1 ]
Zhang, Qihui [1 ]
Bai, Yongcheng [1 ]
Ma, Chen [1 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
基金
中国国家自然科学基金;
关键词
metal-free process; benzoic-fused seven-membered lactams; Smiles rearrangement; DERIVATIVES; INHIBITORS; SERIES; AGENTS;
D O I
10.1021/co300139s
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A facile and efficient method has been developed for the synthesis of a small library of dibenzo[b,f][1,4]thiazepin-11(10H)-ones via Smiles rearrangement. Compounds were obtained in excellent isolated yields (70%-92%) under metal-free conditions. More specifically, this transition metal-free process relates to an environmentally friendly, economical, and efficient method for preparing benzoic-fused seven-membered lactams.
引用
收藏
页码:130 / 134
页数:5
相关论文
共 35 条
  • [1] Heterocycles [h]Fused onto 4-oxoquinoline-3-carboxylic acid, part IV.: Convenient synthesis of substituted hexahydro [1,4]Thiazepino[2,3-h]quinoline-9-carboxylic acid and its tetrahydroquino[7,8-b]benzothiazepine homolog
    Al-Huniti, Mohammed H.
    El-Abadelah, Mustafa M.
    Zahra, Jalal A.
    Sabri, Salim S.
    Ingendoh, Arnd
    [J]. MOLECULES, 2007, 12 (08): : 1558 - 1568
  • [2] 1,5-Benzothiazepine, a versatile pharmacophore: A review
    Bariwal, Jitender B.
    Upadhyay, Kuldip D.
    Manvar, Atul T.
    Trivedi, Jalpa C.
    Singh, Jyoti S.
    Jain, Kishor S.
    Shah, Anarmik K.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) : 2279 - 2290
  • [3] Antiproliferative and Differentiating Activities of a Novel Series of Histone Deacetylase Inhibitors
    Binaschi, Monica
    Boldetti, Andrea
    Gianni, Maurizio
    Maggi, Carlo Alberto
    Gensini, Martina
    Bigioni, Mario
    Parlani, Massimo
    Giolitti, Alessandro
    Fratelli, Maddalena
    Valli, Claudia
    Terao, Mineko
    Garattini, Enrico
    [J]. ACS MEDICINAL CHEMISTRY LETTERS, 2010, 1 (08): : 411 - 415
  • [4] Donati D, 2000, Pharm Acta Helv, V74, P239, DOI 10.1016/S0031-6865(99)00059-X
  • [5] BENZAZEPINONE CALCIUM-CHANNEL BLOCKERS .2. STRUCTURE-ACTIVITY AND DRUG-METABOLISM STUDIES LEADING TO POTENT ANTIHYPERTENSIVE AGENTS - COMPARISON WITH BENZOTHIAZEPINONES
    FLOYD, DM
    KIMBALL, SD
    KRAPCHO, J
    DAS, J
    TURK, CF
    MOQUIN, RV
    LAGO, MW
    DUFF, KJ
    LEE, VG
    WHITE, RE
    RIDGEWELL, RE
    MORELAND, S
    BRITTAIN, RJ
    NORMANDIN, DE
    HEDBERG, SA
    CUCINOTTA, GG
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (04) : 756 - 772
  • [6] Synthesis of novel tricyclic pyrimido[4,5-b][1,4]benzothiazepines via Bischler-Napieralski-type reactions
    Fu, RZ
    Xu, XX
    Dang, Q
    Bai, X
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) : 10810 - 10816
  • [7] EFFECTS OF A TRANQUILIZER AND 2 ANTIDEPRESSANTS ON LEARNED AND UNLEARNED BEHAVIORS
    GEYER, HM
    WATZMAN, N
    BUCKLEY, JP
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1970, 59 (07) : 964 - &
  • [8] Hargrave K. D., 1991, Can. Pat. Appl., Patent No. [CA 2024040 A1, 2024040]
  • [9] Postmortem distribution of the novel antipsychotic drug quetiapine
    Hopenwasser, J
    Mozayani, A
    Danielson, TJ
    Harbin, J
    Narula, HS
    Posey, DH
    Shrode, PW
    Wilson, SK
    Li, R
    Sanchez, LA
    [J]. JOURNAL OF ANALYTICAL TOXICOLOGY, 2004, 28 (04) : 264 - 268
  • [10] A transition metal-free tandem process to pyrrolopyrazino[2,3-d]pyridazine-diones
    Huang, Aiping
    Qiao, Zhi
    Zhang, Xinhai
    Yu, Wei
    Zheng, Qingqing
    Ma, Ying
    Ma, Chen
    [J]. TETRAHEDRON, 2012, 68 (03) : 906 - 912