Regioselective Synthesis of 1,2-Benzothiazine 1,1-Dioxide Derivatives by Intramolecular Heck Cyclization

被引：11

作者：

Debnath, Sudarshan ^{[1
,2
]}

Malakar, Suniti ^{[2
]}

Mondal, Shovan ^{[1
]}

机构：

[1] Univ Burdwan, Dept Chem, Syamsundar Coll, Shyamsundar 713424, India

[2] Visva Bharati Univ, Dept Chem, Santini Ketan 731235, W Bengal, India

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 20期

关键词：

sultams; Heck cyclization; regioselectivity; XRD; CATALYZED TANDEM CYCLIZATION; BENZOSULTAMS; INHIBITORS; SULTAMS; SULFUR;

D O I：

10.1055/s-0035-1562440

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of bioactive heterocycles containing 1,2-benzothiazine 1,1-dioxide derivatives via Pd-catalyzed intramolecular Heck cyclization is reported. The method offers the regioselective synthesis of highly functionalized benzosultams in 80-85% yields. The structure of benzosultam derivatives is confirmed from single crystal X-ray diffraction.

引用

页码：3544 / 3550

页数：7

共 23 条

[1] Antioxidant and antimicrobial studies of novel N′-(substituted-2-chloroquinolin-3-yl)methylidene-4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazides 1,1-dioxides [J].

Ahmad, Matloob ;

Rizvi, Syed Umar Farooq ;

Siddiqui, Hamid Latif ;

Ahmad, Saeed ;

Parvez, Masood ;

Suliman, Ruqia .

MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (09) :2340-2348

[2] A remarkable accelerating effect of Ag-salt on intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides [J].

Barange, Deepak Kumar ;

Nishad, T. C. ;

Swamy, N. Kumara ;

Bandameedi, Venkanna ;

Kumar, Dinesh ;

Sreekanth, Bukkapattanam R. ;

Vyas, K. ;

Pal, Manojit .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8547-8550

[3] Respiratory syncytial virus fusion inhibitors. Part 6: An examination of the effect of structural variation of the benzimidazol-2-one heterocycle moiety [J].

Combrink, Keith D. ;

Gulgeze, H. Belgin ;

Thuring, Jan W. ;

Yu, Kuo-Long ;

Civiello, Rita L. ;

Zhang, Yi ;

Pearce, Bradley C. ;

Yin, Zhiwei ;

Langley, David R. ;

Kadow, Kathleen F. ;

Cianci, Christopher W. ;

Li, Zhufang ;

Clarke, Junius ;

Genovesi, Eugene V. ;

Medina, Ivette ;

Lamb, Lucinda ;

Yang, Zheng ;

Zadjura, Lisa ;

Krystal, Mark ;

Meanwell, Nicholas A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (17) :4784-4790

[4] Regio- and Stereoselective Synthesis of Benzo--sultams by Palladium-Catalyzed Hydrocarbonation of Alkynes [J].

Debnath, Sudarshan ;

Mondal, Shovan .

SYNTHESIS-STUTTGART, 2016, 48 (05) :710-722

[5] One-Pot Sonogashira Coupling-Cyclization toward Regioselective Synthesis of Benzosultams [J].

Debnath, Sudarshan ;

Mondal, Shovan .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) :3940-3948

[6] 1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams [J].

Ishida, Naoki ;

Shimamoto, Yasuhiro ;

Yano, Takaaki ;

Murakami, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (51) :19103-19106

[7] Discovery of cyclicsulfonamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors [J].

Kim, Se Hoan ;

Ramu, Ravirala ;

Kwon, Sung Wook ;

Lee, Su-Hee ;

Kim, Chi Hyun ;

Kang, Seung Kyu ;

Rhee, Sang Dal ;

Bae, Myung Ae ;

Ahn, Sung Hoon ;

Ha, Duck Chan ;

Cheon, Hyae Gyeong ;

Kim, Ki Young ;

Ahn, Jin Hee .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (03) :1065-1069

[8] Phosphine gold(I)-catalyzed hydroamination of alkenes under thermal and microwave-assisted conditions [J].

Liu, Xin-Yuan ;

Li, Cheng-Hui ;

Che, Chi-Ming .

ORGANIC LETTERS, 2006, 8 (13) :2707-2710

[9] Recent Developments in the Synthesis of Fused Sultams [J].

Majumdar, K. C. ;

Mondal, Shovan .

CHEMICAL REVIEWS, 2011, 111 (12) :7749-7773

[10] Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis [J].

McReynolds, MD ;

Dougherty, JM ;

Hanson, PR .

CHEMICAL REVIEWS, 2004, 104 (05) :2239-2258

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