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
  • [31] An I2-mediated aerobic oxidative annulation of amidines with tertiary amines via C-H amination/ C-N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines
    Yan, Yizhe
    Li, Zheng
    Cui, Chang
    Li, Hongyi
    Shi, Miaomiao
    Liu, Yanqi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (15) : 2629 - 2633
  • [32] Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles
    Mashayekh, Siavash
    Rahmanipour, Narges
    Mahmoodi, Behnaz
    Ahmadi, Fatemeh
    Motaharian, Dina
    Shahhosseini, Soraya
    Shafaroodi, Hamed
    Banafshe, Hamid R.
    Shafiee, Abbas
    Navidpour, Latifeh
    BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (06) : 1929 - 1937
  • [33] Iodine-mediated C-N and C-S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles
    Ambethkar, Sethurajan
    Vellimalai, Muthalu
    Padmini, Vediappen
    Bhuvanesh, Nattamai
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) : 75 - 80
  • [34] Synthesis of some new 3-[N9-carbazolylmethyl]-4-(3-chloro-4-substituted aryl-2-oxo-azetidine)-5-mercapto-1,2,4-triazoles :: antifungal and antibacterial agents
    Nema, A.
    Srivastava, S. K.
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION A-PHYSICAL SCIENCES, 2007, 77A : 313 - 319
  • [35] Tertiary amines as a C1 synthon: metal-free synthesis of quinolines and 2-substituted quinolines via [3+2+1] aerobic cyclization and C-N bond cleavage
    Liu, Jing-Yuan
    Wang, Zhen-Ying
    Li, Qiang
    Li, Dacheng
    Dou, Jianmin
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (11) : 5155 - 5159
  • [36] Metal-Free Synthesis of 3-Arylquinolin-2-ones from N,2-Diarylacrylamides via Phenyliodine(III) Bis(2,2-dimethylpropanoate)-Mediated Direct Oxidative C-C Bond Formation
    Cao, Yang
    Zhao, Hui
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (22) : 3610 - 3615
  • [37] Visible-Light-Mediated Synthesis of 4H-benzo[1,4]thiazin-2-amines and 3,4-Dihydroquinoxalin-2-amines: An Efficient and Metal Free Route to C-S, C-N Bond Formation
    Yadav, Neetu
    Sagir, Hozeyfa
    Ansari, Mohd. Danish
    Siddiqui, I. R.
    CATALYSIS LETTERS, 2018, 148 (06) : 1676 - 1685
  • [38] KI/K2S2O8-Mediated C-S/C-N Bond Formation: One-Pot Regioselective Synthesis of 5H-Thiazolo[3,2-a]pyrimidines
    Yang, Zan
    Liu, Si
    Li, An
    Liao, Jiashu
    Li, Lijun
    Yang, Tao
    Zhou, Congshan
    CHEMISTRYSELECT, 2019, 4 (21): : 6583 - 6586
  • [39] Convenient Synthesis of 5-Substituted 2-Amino[1,2,4]triazolo-[1,5-α][1,3,5] triazin-7(6H)-ones from N-Triazolide Imidates and 1,2,4-Triazole-3,5-diamine
    Khankischpur, Mehdi
    Hansen, Finn K.
    Geffken, Detlef
    SYNTHESIS-STUTTGART, 2010, (10): : 1645 - 1648
  • [40] Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione - methanol (1/1), C11H13N5S
    Jia, Huijuan
    Dong, Zhen
    Qin, Xiaoyan
    Song, Yiying
    Zhou, Zhibin
    Yuan, Caixia
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2022, 237 (03): : 403 - 405
12345