Modular Synthesis of 3,6-Disubstituted-1,2,4-triazines via the Cyclodehydration of β-Keto-N-acylsulfonarnides with Hydrazine Salts

被引：11
|
作者：
Dowling, Matthew S. [1 ]
Jiao, Wenhua [1 ]
Hou, Jie [2 ]
Jiang, Yuchun [2 ]
Gong, Shangsheng [2 ]
机构：
[1] Pfizer Inc, Med Design, Eastern Point Rd, Groton, CT 06340 USA
[2] WuXi AppTec, 288 Fute Zhong Rd, Shanghai 200131, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 07期
关键词：
AS-TRIAZINE DERIVATIVES; DIELS-ALDER REACTION; SUBSTITUTED 1,2,4-TRIAZINES; ACID; DISCOVERY; ANALOGS; ACCESS; RING;
D O I：
10.1021/acs.joc.8b00254
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward method for preparing 3,6-disubstituted-1,2,4-triazines through a redox-efficient cyclo-dehydration of beta-keto-N-acylsulfonamides with hydrazine salts is described. Two approaches for synthesizing the requisite beta-keto-N-acylsulfonarnides are presented, which allow for the late stage incorporation of either the C3 or C6 substituent in a flexible manner from acid chlorides or alpha-bromoketones, respectively. The scope of this methodology includes primary and secondary sp(3)-linked substituents at both the C3 and C6 positions, and the mild reaction conditions tolerate a variety of sensitive functionalities.
引用
收藏
页码：4229 / 4238
页数：10
相关论文
共 41 条
  • [31] Synthesis of 5-Trifluoromethyl-1,4-dihydro-1,2,4-triazines via Base-mediated [3+3] Cycloaddition of Nitrile Imines and CF3-Imidoyl Sulfoxonium Ylides
    Sun, Yue
    Ling, Sihao
    Duan, Yubo
    Li, Jingxian
    Chen, Zhengkai
    Wu, Xiao-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) : 1521 - 1525
  • [32] Efficient synthesis of 3,5,6-trisubstituted-1,2,4-triazines in the bronsted acidic ionic liquid, 1-n-butylimidazolium tetrafluoroborate ([Hbim]BF4)
    Potewar, T. M.
    Lahoti, R. J.
    Daniel, Thomas
    Srinivasan, K. V.
    SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 261 - 269
  • [33] Aminovinyl ketones and aminovinyl esters as C-C-N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines
    Charushin, VN
    Mochulskaya, NN
    Andreiko, AA
    Filyakova, VI
    Kodess, MI
    Chupakhin, ON
    TETRAHEDRON LETTERS, 2003, 44 (11) : 2421 - 2424
  • [34] A convenient synthesis of 3,6-disubstituted-1,4-dihydro-[1,2,4,5] tetrazines and preparation of new acetic acid derivatives containing 5-oxo-4-phenylamino-4,5-dihydro-[1,2,4]triazole
    Demirbas, A
    TURKISH JOURNAL OF CHEMISTRY, 2004, 28 (03): : 311 - 323
  • [35] 1,2,4-TRIAZINES .5. REGIOSELECTIVE N2-AMINATION OF 3-METHYLTHIO-1,2,4-TRIAZIN-5(2H)-ONES - A NEW EFFICIENT SYNTHESIS OF [1,2,4]TRIAZOLO[2,3-B][1,2,4]TRIAZIN-7(1H)-ONE
    SANEMITSU, Y
    NAKAYAMA, Y
    SHIROSHITA, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1583 - 1584
  • [36] 1,2,4-TRIAZINES .7. REGIOSELECTIVE N2-AMINATION OF 3-METHYLTHIO-1,2,4-TRIAZIN-5(2H)-ONES - A NOVEL SYNTHESIS OF [1,2,4]TRIAZOLO[2,3-B][12,4]TRIAZINONES AND [1,2,4]TRIAZOLO[2,3-B][1,2,4]-TRIAZINE
    SANEMITSU, Y
    NAKAYAMA, Y
    SHIROSHITA, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (06) : 1671 - 1675
  • [37] Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles via NaH-DMF-Promoted Dehydrogenative Intramolecular N-S Bond Formation
    Antony, Mary P.
    Chakravarthy, Jeevan A. S.
    Ila, Hiriyakkanavar
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4453 - 4460
  • [38] One-pot synthesis of 3,5-disubstituted 1,2,4-thiadiazoles from nitriles and thioamides via I2-mediated oxidative formation of an N-S bond
    Chai, Ling
    Xu, Yuanqing
    Ding, Tao
    Fang, Xiaomin
    Zhang, Wenkai
    Wang, Yanpeng
    Lu, Minghua
    Xu, Hao
    Yang, Xiaobo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (39) : 8410 - 8417
  • [39] 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
  • [40] Synthesis of C3-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind-Srogl Reaction for Fluorogenic Labeling of Live Cells
    Slachtova, Veronika
    Bellova, Simona
    Vrabel, Milan
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 14634 - 14640
12345