Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates

被引：26

作者：

Omar, Mohamed A. ^{[1
]}

Conrad, Juergen ^{[1
]}

Beifuss, Uwe ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

来源：

TETRAHEDRON | 2014年 / 70卷 / 35期

关键词：

Copper; Chromenes; Imidazobenzothiazines; Quinazolines; Domino reaction; ONE-POT SYNTHESIS; DIHYDROFOLATE-REDUCTASE; PNEUMOCYSTIS-CARINII; CASCADE SYNTHESIS; C-N; DERIVATIVES; INHIBITORS; DISCOVERY; APOPTOSIS; BROMIDES;

D O I：

10.1016/j.tet.2014.06.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5682 / 5695

页数：14

共 102 条

[1] ACTIVITY OF ANTIFOLATES AGAINST PNEUMOCYSTIS-CARINII DIHYDROFOLATE-REDUCTASE AND IDENTIFICATION OF A POTENT NEW AGENT [J].

ALLEGRA, CJ ;

KOVACS, JA ;

DRAKE, JC ;

SWAN, JC ;

CHABNER, BA ;

MASUR, H .

JOURNAL OF EXPERIMENTAL MEDICINE, 1987, 165 (03) :926-931

[2]

[Anonymous], 2009, CHEM3D PRO VERSION

[3] SYNTHESIS OF 5-SUBSTITUTED QUINAZOLINES AS POTENTIAL ANTIMALARIAL AGENTS [J].

ASHTON, WT ;

HYNES, JB .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1233-1237

[4] American Society of Clinical Oncology Clinical Practice Guideline Update on Chemotherapy for Stage IV Non-Small-Cell Lung Cancer [J].

Azzoli, Christopher G. ;

Baker, Sherman, Jr. ;

Temin, Sarah ;

Pao, William ;

Aliff, Timothy ;

Brahmer, Julie ;

Johnson, David H. ;

Laskin, Janessa L. ;

Masters, Gregory ;

Milton, Daniel ;

Nordquist, Luke ;

Pfister, David G. ;

Piantadosi, Steven ;

Schiller, Joan H. ;

Smith, Reily ;

Smith, Thomas J. ;

Strawn, John R. ;

Trent, David ;

Giaccone, Giuseppe .

JOURNAL OF CLINICAL ONCOLOGY, 2009, 27 (36) :6251-6266

[5] Synthesis and biological activity of novel antibacterial quinazolines [J].

Bedi, PMS ;

Kumar, V ;

Mahajan, MP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5211-5213

[6] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions [J].

Beletskaya, Irina P. ;

Cheprakov, Andrei V. .

ORGANOMETALLICS, 2012, 31 (22) :7753-7808

[7] Development of a fast and accurate method of 13C NMR chemical shift prediction [J].

Blinov, Kirill A. ;

Smurnyy, Yegor D. ;

Churanova, Tatiana S. ;

Elyashberg, Mikhail E. ;

Williams, Antony J. .

CHEMOMETRICS AND INTELLIGENT LABORATORY SYSTEMS, 2009, 97 (01) :91-97

[8]

Brown D. J., 1967, CHEM HETEROCYCLIC 1, V24, P11

[9] 4H-1-benzopyrans by a tandem SN2-SNAr reaction [J].

Bunce, Richard A. ;

Rogers, David ;

Nago, Takahiro ;

Bryant, Scott A. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (02) :547-550

[10] Dual kinase inhibition in the treatment of breast cancer: Initial experience with the EGFR/ErbB-2 inhibitor lapatinib [J].

Burris, HA .

ONCOLOGIST, 2004, 9 :10-15

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