Silver-Catalyzed Synthesis of 5-Amino-4-sulfonyl Pyrazoles from 1,2-Diaza-1,3-dienes

被引：0

作者：

Jaiswal, Arvind Kumar ^{[1
]}

Kushawaha, Ajay Kishor ^{[1
]}

Katiyar, Sarita ^{[1
,2
]}

Ansari, Alisha ^{[1
,2
]}

Bhatt, Hemlata ^{[1
,2
]}

Kant, Ruchir ^{[3
]}

Sashidhara, Koneni V. ^{[1
,2
,4
]}

机构：

[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India

[2] Acad Sci & Innovat Res, Ghaziabad 201002, Uttar Pradesh, India

[3] CSIR Cent Drug Res Inst, Mol & Struct Biol, Lucknow 226031, India

[4] CSIR Cent Drug Res Inst, Sophisticated Analyt Instrument Facil & Res, Lucknow 226031, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 21期

关键词：

SULFONYL; ALKYNES; IODINE; DESIGN; METAL;

D O I：

10.1021/acs.joc.4c01936

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and dependable synthetic route for 5-amino-4-sulfonyl pyrazoles, which are substantially important in pharmaceuticals, is highly desirable. This work presents a novel cascade reaction for their efficient synthesis. The approach utilizes silver as a catalyst for C(sp2)-H sulfonylation of readily available starting materials 1,2-diaza-1,3-dienes with sulfinate salts, followed by intramolecular cascade cyclization annulation to afford the desired 5-amino-4-sulfonyl pyrazoles in good to excellent yields under mild conditions.

引用

页码：16033 / 16037

页数：5

共 12 条

[1] Powerful Approach to Heterocyclic Skeletal Diversity by Sequential Three-Component Reaction of Amines, Isothiocyanates, and 1,2-Diaza-1,3-dienes
Attanasi, Orazio A.
Bartoccini, Silvia
Favi, Gianfranco
Giorgi, Gianluca
Perrulli, Francesca Romana
Santeusanio, Stefania
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) : 1161 - 1167
[2] Silver-catalyzed Regioselective Synthesis of N-aryl-1H-pyrazolyl-substituted Benzenesulfonamides from Ynamides and Pyrazoles
Karunakar, Galla V.
Raju, Chittala Emmaniel
Himaja, Karra Sai Bhavani Nagasri
Kumar, Perla Bharath
Sridhar, Balasubramanian
CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (15)
[3] Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2′-Oxo-imidazo[ 1′,5′-f]tetrahydropyridazine
Attanasi, Orazio A.
Bianchi, Luca
D'Auria, Maurizio
Favi, Gianfranco
Mantellini, Fabio
Racioppi, Rocco
CURRENT ORGANIC SYNTHESIS, 2013, 10 (06) : 951 - 960
[4] Silver-catalyzed highly efficient synthesis of pyrido[1,2-a]pyrimidin-4-ones from 2-aminopyridines and alkynoates
Chen, Zhengwang
Wen, Yuelu
Ding, Hao
Luo, Guotian
Ye, Min
Liu, Liangxian
Xue, Jun
TETRAHEDRON LETTERS, 2017, 58 (01) : 13 - 16
[5] Synthesis of the Phenanthrene and Cyclohepta[a]naphthalene Skeletons via Gold(I)-Catalyzed Intramolecular Cyclization of Unactivated Cyclic 5-(2-Arylethyl)-1,3-dienes
Yeh, Ming-Chang P.
Lin, Ming-Nan
Chou, Yi-Shiang
Lin, Tern-Chi
Tseng, Li-Yu
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 4027 - 4033
[6] Gold/silver-catalyzed synthesis of functionalized indoles from N-allyl-2-alkynylanilines and α-diazo compounds via 1,3-allyl migration
Thakur, Deepika
Meena, Shivam A.
Sharma, Manvi
Verma, Akhilesh K.
CHEMICAL COMMUNICATIONS, 2025, 61 (28) : 5313 - 5316
[7] A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylselanyl)but-1-yne via Palladium-Catalyzed Silylstannylation and Selenoxide Elimination
Shintaku, Kazuki
Maeda, Hajime
Segi, Masahito
SYNTHESIS-STUTTGART, 2013, 45 (03): : 341 - 346
[8] A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide
Rajasekar, Shanmugam
Anbarasan, Pazhamalai
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) : 4563 - 4567
[9] Pseudopericyclic Dearomative 1,6-Cyclization of 1-(2-Pyridyl)-2-azabuta-1,3-dienes: Synthesis and Ring-Chain Valence Equilibria of 4H-Pyrido[1,2-a]pyrazines
Filippov, Ilya P.
Novikov, Mikhail S.
Khlebnikov, Alexander F.
Rostovskii, Nikolai V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (19) : 2904 - 2913
[10] Palladium-Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3-Dienes via CH Bond Activation: Efficient Access to 3,4-Dihydroisocoumarin and 5,6-Dihydrocoumalins
Sun, Youwen
Zhang, Guozhu
CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (08) : 708 - 711

← 1 2 →