Furan recyclization reaction as a new approach to isochromenes

被引:12
作者
Butin, Alexander V. [1 ]
Abaev, Vladimir T. [2 ]
Mel'chin, Vladimir V. [1 ]
Dmitriev, Artem S. [1 ]
Pilipenko, Arkady S. [1 ]
Shashkov, Alexander S. [3 ]
机构
[1] Kuban State Univ Technol, Res Inst Heterocycl Cpds Chem, Krasnodar 350072, Russia
[2] N Ossetian State Univ, Vladikavkaz 362025, Russia
[3] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
来源
SYNTHESIS-STUTTGART | 2008年 / 11期
关键词
furans; ring-opening; ring-closure; fused ring system; isochromene;
D O I
10.1055/s-2008-1072580
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
As part of our ongoing interest in the synthesis of benzannelated heterocycles from o-substituted benzylfurans, recyclization of [o-(hydroxymethyl)aryl] difuryl methanes was studied. It was shown that, under acidic conditions, the o-hydroxymethyl group in these compounds acts as a nucleophile and tetracyclic isochromene derivatives are formed via a recyclization-cyclization tandem sequence. Alternatively, these compounds can be synthesized by reduction of the corresponding isochromone derivatives with lithium aluminum hydride. The potent biologically active analogues of cannabinoids were also obtained by interaction of isochromone derivatives with excess of methylmagnesium iodide.
引用
收藏
页码:1798 / 1804
页数:7
相关论文
共 34 条
[1]   Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes [J].
Abaev, Vladimir T. ;
Dmitriev, Artem S. ;
Gutnov, Andrey V. ;
Podelyakin, Sergey A. ;
Butin, Alexander V. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) :1195-1204
[2]   BENZISOCHROMANQUINONES AND AN ISOFURANONAPHTHOQUINONE FROM VENTILAGO-VITIENSIS (RHAMNACEAE) [J].
ALI, S ;
READ, RW ;
SOTHEESWARAN, S .
PHYTOCHEMISTRY, 1994, 35 (04) :1029-1032
[3]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[4]  
BEGASSE B, 1979, TETRAHEDRON LETT, P2149
[5]  
BETTOLO M, 1965, TETRAHEDRON LETT, P4857
[6]   Synthesis of the 4,10-dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one system by a furan recyclization reaction [J].
Butin, Alexander V. ;
Dmitriev, Artem S. ;
Kostyukova, Olga N. ;
Abaev, Vladimir T. ;
Trushkov, Igor V. .
SYNTHESIS-STUTTGART, 2007, 14 (14) :2208-2214
[7]   Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction [J].
Butin, Alexander V. ;
Smirnov, Sergey K. ;
Stroganova, Tatyana A. ;
Bender, Wolfgang ;
Krapivin, Gennady D. .
TETRAHEDRON, 2007, 63 (02) :474-491
[8]   Synthesis and some transformations of new 9-furylnaphtho[2,3-b]furan derivatives [J].
Butin, Alexander V. ;
Mel'chin, Vladimir V. ;
Abaev, Vladimir T. ;
Bender, Wolfgang ;
Pilipenko, Arkady S. ;
Krapivin, Gennady D. .
TETRAHEDRON, 2006, 62 (34) :8045-8053
[9]   Furan ring opening-isochromene ring closure: a new approach to isochromene ring synthesis [J].
Butin, AV ;
Abaev, VT ;
Mel'chin, VV ;
Dmitriev, AS .
TETRAHEDRON LETTERS, 2005, 46 (48) :8439-8441
[10]   Acid catalyzed reactions of substituted salicylaldehydes with 2-methylfuran [J].
Butin, AV ;
Gutnov, AV ;
Abaev, VT ;
Krapivin, GD .
MOLECULES, 1999, 4 (02) :52-61