Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: the stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides

被引：6
|
作者：
Mondal, Debasmita [1 ]
Pal, Gargi [1 ]
Chowdhury, Chinmay [1 ]
机构：
[1] CSIR Indian Inst Chem Biol, Organ & Med Chem Div, Kolkata 70032, India
来源：
CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 44期
关键词：
Acetylenic carbons - Benzamides - Biologically active compounds - Propargyl carbonates - Regio-selective - Stereoselective formation - Stereoselective synthesis - Sulphonamides;
D O I：
10.1039/d1cc00793a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Pd(0) catalysed cyclisation reactions between tert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides deliver 1,4-benzodiazepin-5-ones or sultam derivatives, key components of many biologically active compounds. But 2-amino benzamides/sulphonamides require propargyl carbonates substituted at acetylenic carbon to undergo the reaction resulting in the stereoselective formation of the said products.
引用
收藏
页码：5462 / 5465
页数：4
相关论文
共 10 条
  • [1] Ring Contraction of 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-Dioxides: Access to 4H-Benzo[b][1,4]thiazine 1,1-Dioxides
    Fueloepova, Veronika
    Krchnakova, Anna
    Schuetznerova, Eva
    Zajicek, Jaroslav
    Krchnak, Viktor
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1795 - 1801
  • [2] Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions
    Trapani, Patricia
    Volna, Tereza
    Soural, Miroslav
    [J]. ACS COMBINATORIAL SCIENCE, 2016, 18 (06) : 349 - 354
  • [3] SYNTHESIS OF SUBSTITUTED INDOLO[3,2-B][1,4]BENZODIAZEPIN-5-ONES AND 1-ARYLIMIDAZO[4,5-B]INDOL-2(1H)-ONES
    HIREMATH, SP
    HIREMATH, DM
    PUROHIT, MG
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1987, 26 (11): : 1042 - 1046
  • [4] Synthesis of 2,3,5,6-tetrahydro-4H-1,4-thiazin-3-one 1,1-dioxides from methyl (styrylsulfonyl)acetate
    Takahashi, M
    Yuda, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (02) : 235 - 238
  • [5] Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4] oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection-lactonization reactions
    AL-Shuaeeb, Riyadh Ahmed Atto
    Galvani, Gilles
    Bernadat, Guillaume
    Brion, Jean-Daniel
    Alami, Mouad
    Messaoudi, Samir
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (44) : 10904 - 10916
  • [6] Synthesis of 5-Amino-3,3-dimethyl-7-phenyl-3H-[1,2]oxathiolo[4,3-b]pyridine-6-carbonitrile 1,1-Dioxides
    Chioua, Mourad
    Samadi, Abdelouahid
    Postel, Denis
    Balzarini, Jan
    Marco-Contelles, Jose
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1452 - 1456
  • [7] A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-c]pyran-1-ones, Indolo[3,2-c]pyran-1-ones, Thieno[2,3-c]pyran-7-ones and Pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction
    Jismy, Badr
    Cherry, Khalil
    Maaliki, Carine
    Ngi, Samuel Inack
    Abarbri, Mohamed
    [J]. MOLECULES, 2020, 25 (21):
  • [8] 4H-1,2,4-pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors:: Design, synthesis, pharmacology, and structure-activity relationships
    Pirotte, B
    Podona, T
    Diouf, O
    de Tullio, P
    Lebrun, P
    Dupont, L
    Somers, F
    Delarge, J
    Morain, P
    Lestage, P
    Lepagnol, J
    Spedding, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (16) : 2946 - 2959
  • [9] Solid-Phase Synthesis of Trisubstituted Benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepin-6(5H)-ones and Their Sulfonyl Analogues under Mild Reaction Conditions
    Fueloepova, Veronika
    Funk, Petr
    Popa, Igor
    McMaster, Claire
    Soural, Miroslav
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (16) : 3551 - 3557
  • [10] CYCLOMETALLATED DERIVATIVES OF PALLADIUM(II) WITH 1,4-BENZODIAZEPIN-2-ONES - CRYSTAL-STRUCTURE OF (L-H)PD(PPH3)CL.CHCL3 (L = PRAZEPAM-7-CHLORO-1-CYCLOPROPYLMETHYL-1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE) - SYNTHESIS OF ISOINDOLO[2,1-D][1,4]BENZODIAZEPINE DERIVATIVES BY REACTION OF [(L-H)PDCL]2 SPECIES WITH CARBON-MONOXIDE
    CINELLU, MA
    GLADIALI, S
    MINGHETTI, G
    STOCCORO, S
    DEMARTIN, F
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 401 (03) : 371 - 384
1