Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives

被引:122
作者
Achari, B [1 ]
Mandal, SB [1 ]
Dutta, PK [1 ]
Chowdhury, C [1 ]
机构
[1] Indian Inst Chem Biol, Div Med Chem, Kolkata 700032, W Bengal, India
关键词
1.4-benzodioxin; 1.4-benzoxazine; biological significance; natural products; syntheses; palladium catalyst; synthetic intermediates;
D O I
10.1055/s-2004-834816
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The origin and growth of the chemistry of 1,4-benzodioxins. 1,4-benzoxazines and their 2.3-dihydro derivatives are briefly described. This class of compounds has attracted special attention due to their natural occurrence and important biological activities. The structural scaffolds of these heterocycles serve as building blocks in various useful syntheses. The introduction of palladium-catalyzed reactions has added a new dimension to this field by making the synthesis more convenient and general. The purpose of this account is to facilitate and revitalize interest in this field within the synthetic community.
引用
收藏
页码:2449 / 2467
页数:19
相关论文
共 104 条
[1]  
ADAM W, 1982, SYNTHESIS-STUTTGART, P322
[2]   SYNTHESIS, THERMAL-STABILITY, AND CHEMI-LUMINESCENCE PROPERTIES OF THE DIOXETANES DERIVED FROM 1,4-DIOXINS [J].
ADAM, W ;
PETERS, EM ;
PETERS, K ;
PLATSCH, H ;
SCHMIDT, E ;
VONSCHNERING, HG ;
TAKAYAMA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3920-3928
[3]   CYTOTOXIC FLAVONOLIGNANS AND FLAVONES FROM VERBASCUM-SINAITICUM LEAVES [J].
AFIFI, MSA ;
AHMED, MM ;
PEZZUTO, JM ;
KINGHORN, AD .
PHYTOCHEMISTRY, 1993, 34 (03) :839-841
[4]   Novel concise synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines by ring opening of glycidols under solid-liquid phase transfer catalysis conditions [J].
Albanese, D ;
Landini, D ;
Penso, M .
CHEMICAL COMMUNICATIONS, 1999, (20) :2095-2096
[5]   Flow injection analysis of doxazosin mesylate using UV-detection [J].
Altiokka, G ;
Atkosar, Z .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2002, 27 (05) :841-844
[6]   ANALOGS OF THE CYCLIC HYDROXAMIC ACID 2,4-DIHYDROXY-7-METHOXY-2H-1,4-BENZOXAZIN-3-ONE - DECOMPOSITION TO BENZOXAZOLINONES AND REACTION WITH BETA-MERCAPTOETHANOL [J].
ATKINSON, J ;
MORAND, P ;
ARNASON, JT ;
NIEMEYER, HM ;
BRAVO, HR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1788-1800
[7]  
BARTSCH H, 1982, J HETEROCYCLIC CHEM, V19, P1189, DOI 10.1002/jhet.5570190540
[8]   STUDIES ON THE CHEMISTRY OF 1,4-OXAZINES .12. 2,3-DIBROMO-3,4-DIHYDRO H-4-1,4-BENZOXAZINES AND THEIR NUCLEOPHILIC DISPLACEMENT-REACTIONS - THE 1ST SYNTHESIS OF 4-ACETYL-H-4-1,4-BENZOXAZINE-3-CARBONITRILE [J].
BARTSCH, H ;
OFNER, M ;
SCHWARZ, O ;
THOMANN, W .
HETEROCYCLES, 1984, 22 (12) :2789-2797
[9]   Palladium mediated regio- and stereoselective synthesis of exomethylene benzo- and naphthodioxans [J].
Basak, A ;
Bhattacharya, G ;
Mallik, UK ;
Khamrai, UK .
SYNTHETIC COMMUNICATIONS, 1997, 27 (03) :367-373
[10]   3-PHENYL-2H-1,4-BENZOXAZINE-4-OXIDES .1. SYNTHESIS AND REDUCTION [J].
BATTISTONI, P ;
BRUNI, P ;
FAVA, G .
TETRAHEDRON, 1979, 35 (14) :1771-1775