Acid-Mediated Intramolecular Cyclizations of (N-Aryl)-acetylenic Sulfonamides: Synthesis of Fused and Spirocyclic Sultams

被引:1
作者
Reddy, Chada Raji [1 ,2 ]
Rathaur, Anjali [1 ,2 ]
Sagar, Banoth Karuna [1 ,2 ]
机构
[1] CSIR Indian Inst Chem Technol IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
2,1-BENZOTHIAZINE 2,2-DIOXIDE; DERIVATIVES; INHIBITORS; SULFUR;
D O I
10.1021/acs.joc.4c01517
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report acid-mediated divergent annulations of (N-aryl)-alkynyl sulfonamides. The substituent at the para position of the N-aryl group determines two diverse reaction paths, leading to the selective assembly of benzo-fused sultams and spirocyclic sultams. This strategy provides a series of benzo/spiro-sultams with wide functional group compatibility and good to excellent yields under mild reaction conditions. Additionally, scale-up reaction and further transformations of the products were also carried out to demonstrate the utility of the protocol.
引用
收藏
页码:14120 / 14128
页数:9
相关论文
共 53 条
  • [1] Ager DJ, 1998, ANGEW CHEM INT EDIT, V37, P1803
  • [2] Synthesis of chiral benzosultams: 3-functionalized 1,2-benzisothiazoline 1,1-dioxides
    Ahn, KH
    Baek, HH
    Lee, SJ
    Cho, CW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) : 7690 - 7696
  • [3] Stronger Bronsted Acids: Recent Progress
    Akiyama, Takahiko
    Mori, Keiji
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9277 - 9306
  • [4] Synthesis of Azaspiro Tricyclic Scaffolds through Post-Ugi Modifications: Scope and Limitation of Aza-Michael Cyclization
    Ambule, Mayur D.
    Bhumij, Mandweep
    Kumar, Asheesh
    Kant, Ruchir
    Kumar Srivastava, Ajay
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (10)
  • [5] Anderson D. J., 2001, WO Patent, Patent No. [1378546A, 1378546]
  • [6] Sulfonamides and Sulfonylated Derivatives as Anticancer Agents
    Casini, Angela
    Scozzafava, Andrea
    Mastrolorenzo, Antonio
    Supuran, Claudiu T.
    [J]. CURRENT CANCER DRUG TARGETS, 2002, 2 (01) : 55 - 75
  • [7] Visible-light induced dearomatization reactions
    Cheng, Yuan-Zheng
    Feng, Zuolijun
    Zhang, Xiao
    You, Shu-Li
    [J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (06) : 2145 - 2170
  • [8] Sulfonamides: Antiviral Strategy for Neglected Tropical Disease Virus
    Dash, Rudra Narayan
    Moharana, Alok Kumar
    Subudhi, Bharat Bhusan
    [J]. CURRENT ORGANIC CHEMISTRY, 2020, 24 (09) : 1018 - 1041
  • [9] One-Pot Sonogashira Coupling-Cyclization toward Regioselective Synthesis of Benzosultams
    Debnath, Sudarshan
    Mondal, Shovan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 3940 - 3948
  • [10] Sulfur-Containing Agrochemicals
    Devendar, Ponnam
    Yang, Guang-Fu
    [J]. TOPICS IN CURRENT CHEMISTRY, 2017, 375 (06)