I2-Mediated Oxidative C-N and N-S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

被引：46
|
作者：
Jatangi, Nagesh [1 ]
Tumula, Nagaraju [1 ]
Palakodety, Radha Krishna [1 ]
Nakka, Mangarao [1 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 10期
关键词：
ONE-POT SYNTHESIS; MOLECULAR-IODINE; ANTIFUNGAL AGENTS; 1,2,4-TRIAZOLES; DERIVATIVES; 1,2,4-THIADIAZOLES; DIMERIZATION; EFFICIENT;
D O I：
10.1021/acs.joc.8b00753
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An environmentally benign and convenient strategy for the synthesis of 4,5-disubstituted/N-fused 3-amino-1,2,4-triazoles and 3-substituted 5-amino-1,2,4-thiadiazoles from isothiocyanates has been developed. This metal-free method involves I-2-mediated oxidative C-N and N-S bond formations in water. Furthermore, this facile protocol exhibited excellent substrate tolerance in good to high yields and scalable fashion.
引用
收藏
页码：5715 / 5723
页数：9
相关论文
共 43 条
  • [21] N-Carbamimidoyl-2,2,2-Trifluoro-N′-Arylacetimidamides as Important Intermediates for the Synthesis of 3-Amino-4-Aryl-5-(Trifluoromethyl)-1H-1,2,4-Triazoles
    Abdinasab, Salimeh
    Darehkordi, Ali
    Abbasi, Alireza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, : 240 - 248
  • [22] Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3-and 1,2,4-Triazoles from Bisarylhydrazones via C-H Functionalization/C-C/N-N/C-N Bonds Formation
    Guru, Murali Mohan
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) : 5063 - 5073
  • [23] I2-Mediated Oxidative C-N Bond Formation for Metal-Free One-Pot Synthesis of Di-, Tr-, and Tetrasubstituted Pyrazoles from α,β-Unsaturated Aldehydes/Ketones and Hydrazines
    Zhang, Xinting
    Kang, Jinfeng
    Niu, Pengfei
    Wu, Jie
    Yu, Wenquan
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10170 - 10178
  • [24] Co-Catalyzed Intramolecular S-N Bond Formation in Water for 1,2-Benzisothiazol-3(2H)-ones and 1,2,4-Thiadiazoles Synthesis
    Yang, Liting
    Song, Lijuan
    Tang, Shanyu
    Li, Longjia
    Li, Heng
    Yuan, Bingxin
    Yang, Guanyu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (06) : 1281 - 1285
  • [25] Electrochemical Synthesis of 3,5-Bis(acyl)-1,2,4-thiadiazoles through n-Bu4NI-mediated Oxidative Dimerization of α-Oxothioamides
    Shivaraj, Mahadev
    Suresh, Rajaghatta N.
    Swaroop, Toreshettahally R.
    Kumara, Manikyanahally N.
    Rangappa, Kanchugarakoppal S.
    Mantelingu, Kempegowda
    Mamatha Devi, Adaganahalli Boregowda
    Manasa, Madihalli Prasanna
    Umashankara, Muddegowda
    ELECTROCHEMISTRY, 2023, 91 (12)
  • [26] A mild and efficient synthesis of 4,5-disubstituted 3-amino-4-hydroxythiazo-lidine-2-thiones and S,N-disubstituted 1,3,4-thiadiazole-2-thiones
    Ge, ZM
    Cui, JL
    Wang, YL
    Cheng, TM
    Li, RT
    SYNTHESIS-STUTTGART, 2004, (08): : 1257 - 1261
  • [27] Metal-free C-N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5′]thiazolo- and thiazolo [2′,3′:2,3]imidazo[4,5-c]cinnolines
    Kandimalla, Satheeshkumar Reddy
    Sabitha, Gowravaram
    RSC ADVANCES, 2016, 6 (71): : 67086 - 67095
  • [28] A Simple and Efficient Synthesis of 3,4,5-Trisubstituted/N-Fused 1,2,4-Triazoles via Ceric Ammonium Nitrate Catalyzed Oxidative Cyclization of Amidrazones with Aldehydes Using Polyethylene Glycol as a Recyclable Reaction Medium
    Nakka, Mangarao
    Tadikonda, Ramu
    Rayavarapu, Srinuvasarao
    Sarakula, Prasanthi
    Vidavalur, Siddaiah
    SYNTHESIS-STUTTGART, 2015, 47 (04): : 517 - 525
  • [29] Iodine-mediated oxidative N-S bond formation: a facile one-pot synthetic approach to 1,2,4-benzothiadiazine 1,1-dioxides under transition metal-free conditions
    Ugur, Sumeyye Buran
    Dogan, Sengul Dilem
    JOURNAL OF SULFUR CHEMISTRY, 2023, 44 (03) : 354 - 360
  • [30] SYNTHESIS OF SOME N-ALKYLATED 1,2,4-TRIAZOLES, 1,3,4-OXADIAZOLES, AND 1,3,4-THIADIAZOLES BASED ON N-(FURAN-2-YL-METHYLIDENE)-4,6-DIMETHYL-1H-PYRAZOLO-[3,4-b]PYRIDINE-3-AMINE
    El-Essawy, F. A.
    Rady, S. I. M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (04) : 497 - 506
12345