Concise synthesis of phenanthrene derivatives via intermolecular TDDA reaction induced by tetrayne cyclization

被引：1

作者：

Liu, Baohua ^{[1
]}

Cao, Xiujun ^{[1
]}

Yan, Jingjing ^{[1
]}

Hu, Qiong ^{[2
]}

Hu, Yimin ^{[2
]}

机构：

[1] Anhui Univ Sci & Technol, Sch Chem Engn, State Prevent & Control Deep Coal Mines, Huainan 232001, Peoples R China

[2] Anhui Normal Univ, Sch Chem & Mat Sci, Wuhu 241002, Anhui, Peoples R China

来源：

TETRAHEDRON LETTERS | 2022年 / 99卷

基金：

中国国家自然科学基金;

关键词：

Phenanthrene; Tetradehydro-Diels-Alder; Benzyne; Hexadehydro-Diels-Alder; Naphthalene; Chemoselectivity; ARYNES; REARRANGEMENT; CONSTRUCTION; GENERATION; CHEMISTRY; VERSATILE; BENZYNES; ALKYNES; SILVER; ACIDS;

D O I：

10.1016/j.tetlet.2022.153850

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile construction of phenanthrene derivatives through the intermoletetradehydro-Diels-Alder (TDDA) reaction of benzyne in situ generated by the hexadehydro-Diels-Alder (HDDA) reaction with various substituted phenylacetylene was described. The naphthalene derivatives were obtained unexpectedly in another reaction modle when expanding substrate scope. The reaction profiles has good chemoselectivity and provided a new way for the synthesis of highly functionalized phenanthrene and naphthalene derivatives from simple materials under relatively mild conditions. (C) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

共 62 条

[1]

[Anonymous], 1952251 CCDC

[2] The larger acenes: Versatile organic semiconductors [J].

Anthony, John E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483

[3] Synthesis of complex benzenoids via the intermediate generation of o-benzynes through the hexadehydro-Diels-Alder reaction [J].

Baire, Beeraiah ;

Niu, Dawen ;

Willoughby, Patrick H. ;

Woods, Brian P. ;

Hoye, Thomas R. .

NATURE PROTOCOLS, 2013, 8 (03) :501-508

[4] STUDIES IN THE WAGNER REARRANGEMENT .4. THE STERIC EFFECT OF AN ORTHO-METHYL GROUP [J].

BENJAMIN, BM ;

COLLINS, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (02) :402-405

[5] ANTIMICROBIAL AND ANTITUMOR PROPERTIES OF 9,10-DIHYDROPHENANTHRENES: STRUCTURE ACTIVITY STUDIES ON JUNCUSOL [J].

BOGER, DL ;

MITSCHER, LA ;

MULLICAN, MD ;

DRAKE, SD ;

KITOS, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (10) :1543-1547

[6] REGIOSPECIFIC TOTAL SYNTHESIS OF JUNCUSOL [J].

BOGER, DL ;

MULLICAN, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4045-4050

[7] Dehydration of 9-fluorenylcarbinol: A new synthesis of phenanthrene [J].

Brown, WG ;

Bluestein, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :3256-3257

[8] Conversion of 2,7-dibromofluorene to 2,7-dibromophenanthrene [J].

Brown, WG ;

Bluestein, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1235-1237

[9] STUDIES IN THE WAGNER REARRANGEMENT .6. THE DIRECTIVE EFFECTS OF THE METHYL AND METHOXYL GROUPS [J].

COLLINS, CJ ;

BENJAMIN, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (07) :1644-1647

[10] Regioselective Synthesis of Substituted Cyclopenta[l]phenanthrenes [J].

Connors, David M. ;

Goroff, Nancy S. .

ORGANIC LETTERS, 2016, 18 (17) :4262-4265

← 1 2 3 4 5 6 7 →