I2/K2S2O8-Promoted ring-opening cyclizations of benzothiazoles and 3-oxo-3-arylpropanenitriles

被引：6

作者：

Li, Xuezhen ^{[1
]}

He, Jing ^{[1
]}

Du, Mingxi ^{[1
]}

Zhang, Jie ^{[1
]}

Gu, Yanlong ^{[2
]}

Vaccaro, Luigi ^{[3
]}

Liu, Ping ^{[1
]}

机构：

[1] Shihezi Univ, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Sch Chem & Chem Engn, Shihezi 832004, Peoples R China

[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Mat Chem & Serv Failure, Minist Educ,Key Lab Mat Chem Energy Convers & Sto, Wuhan 430074, Peoples R China

[3] Univ Perugia, Dipartimento Chim Biol & Biotecnol, Lab Green SOC, Perugia, Italy

来源：

MOLECULAR CATALYSIS | 2022年 / 517卷

基金：

中国国家自然科学基金;

关键词：

I-2-Catalyzed; Ring-opening cyclization; Benzothiazole; 3-oxo-3-arylpropanenitrile; 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitrile; ONE-POT SYNTHESIS; 1,4-BENZOTHIAZINE; DERIVATIVES; 1,4-BENZOXAZINE; 2-AMINOBENZOTHIAZOLES; CONVERSION; EXPANSION; ANALOGS; ACIDS;

D O I：

10.1016/j.mcat.2021.112051

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient I-2/K2S2O8-promoted ring expansion of benzo[d]thiazole and 3-oxo-3-arylpropanenitrile has been developed. A variety of benzo[d]thiazole derivatives underwent the ring-opening cyclization smoothly to afford the diverse 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitriles in moderate to excellent yields. This protocol features metal-free reaction conditions, stable and available starting materials, and good group tolerance. The synthetic utility of this protocol was also demonstrated through gram-scale reaction and product derivatization. Mechanism studies indicate that the reaction may undergo a free radical process.

引用

页数：6

共 31 条

[1] Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)
Aiello, Stefania
Wells, Geoffrey
Stone, Erica L.
Kadri, Hachemi
Bazzi, Rana
Bell, David R.
Stevens, Malcolm F. G.
Matthews, Charles S.
Bradshaw, Tracey D.
Westwell, Andrew D.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) : 5135 - 5139
[2] Practical and Efficient Synthesis of 3-Aryl-2H-benzo[1,4]thiazine Derivatives Catalyzed by KHSO4
Baghernejad, Bita
Heravi, Majid M.
Oskooie, Hossein A.
[J]. SYNTHETIC COMMUNICATIONS, 2011, 41 (04) : 589 - 593
[3] Iron-catalyzed microwave-promoted expeditious one-pot synthesis of benzo[b][1,4]thiazine-4-carbonitrile under solvent-free condition
Balwe, Sandip Gangadhar
Shinde, Vijay Vilas
Jeong, Yeon Tae
[J]. TETRAHEDRON LETTERS, 2016, 57 (46) : 5074 - 5078
[4] 1,4-BENZOTHIAZINE-2-CARBOXYLIC ACID 1-OXIDES AS ANALOGS OF ANTIBACTERIAL QUINOLONES
CECCHETTI, V
FRAVOLINI, A
SCHIAFFELLA, F
TABARRINI, O
ZHOU, WC
PAGELLA, PG
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (02) : 375 - 382
[5] QUINOLONECARBOXYLIC ACIDS .2. SYNTHESIS AND ANTIBACTERIAL EVALUATION OF 7-OXO-2,3-DIHYDRO-7H-PYRIDO[1,2,3-DE][1,4]BENZOTHIAZINE-6-CARBOXYLIC ACIDS
CECCHETTI, V
FRAVOLINI, A
FRINGUELLI, R
MASCELLANI, G
PAGELLA, P
PALMIOLI, M
SEGRE, G
TERNI, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (03) : 465 - 473
[6] Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of 1,4-Benzothiazines
Chu, Jing-Jing
Hu, Bo-Lun
Liao, Zhi-Yong
Zhang, Xing-Guo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18) : 8647 - 8652
[7] MECHANISM OF ACTION AND ANTITUMOR-ACTIVITY OF (S)-10-(2,6-DIMETHYL-4-PYRIDINYL)-9-FLUORO-3-METHYL-7-OXO-2,3-DIHYDRO-7H-PYRIDOL[1,2,3-DE]-[1,4]BENZOTHIAZINE-6-CARBOXYLIC ACID (WIN-58161)
COUGHLIN, SA
DANZ, DW
ROBINSON, RG
KLINGBEIL, KM
WENTLAND, MP
CORBETT, TH
WAUD, WR
ZWELLING, LA
ALTSCHULER, E
BALES, E
RAKE, JB
[J]. BIOCHEMICAL PHARMACOLOGY, 1995, 50 (01) : 111 - 122
[8] Synthesis of Benzo[1,4]thiazines via Ring Expansion of 2-Aminobenzothiazoles with Terminal Alkynes Under Metal-Organic Framework Catalysis
Dang, Ha V.
Le, Y. T. N.
Tran, Duyen T. M.
Phan, Anh N. Q.
Phan, Nam T. S.
[J]. CATALYSIS LETTERS, 2018, 148 (05) : 1383 - 1395
[9] David J., 1988, J PSYCHOPHARMACOL, V12, P283
[10] An Efficient One-Pot Synthesis of Benzo[1,4]Thiazines, Benzo[1,3]Thiazoles and Benzo[1,5] Thiazepines
El-Mahdy, Ahmed F. M.
Mohamed, Omima S.
El-Sherief, Hassan A. H.
Hozien, Zeinab A.
[J]. CURRENT ORGANIC SYNTHESIS, 2017, 14 (04) : 604 - 611

← 1 2 3 4 →