Nitrobutadienes from β-nitrothiophenes:: valuable building-blocks in the overall ring-opening/ring-closure protocol to homo- or hetero-cycles

被引:41
作者
Bianchi, Lara
Dell'Erba, Carlo
Maccagno, Massimo
Morganti, Stefano
Petrillo, Giovanni [1 ]
Rizzato, Egon
Sancassan, Fernando
Severi, Elda
Spinelli, Domenico
Tavani, Cinzia
机构
[1] Univ Genoa, Dipartimento Chim & Chim Ind, Via Dodecaneso 31, I-16146 Genoa, Italy
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy
关键词
nitrothiophenes; ring-opening; ring-closure; heterocycles; nitrobutadienes; isoxazoles;
D O I
10.3998/ark.5550190.0007.714
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Nitrothiophenes undergo a facile ring-opening process when treated with secondary amines in ethanol ( in the presence of AgNO3, but for 3,4-dinitrothiophene), providing interesting polyfunctionalized linear nitro- or dinitro-butadienic building-blocks, which can be further manipulated and eventually exploited for the preparation of targets of various nature. In particular, a great variety of homo- and hetero-cyclic compounds may be obtained and some representative results in this field, relevant to synthetic, mechanistic and stereochemical aspects, are reported herein.
引用
收藏
页码:169 / 185
页数:17
相关论文
共 27 条
[11]  
Consiglio G, 1997, GAZZ CHIM ITAL, V127, P753
[12]  
Dell'Erba C, 1999, EUR J ORG CHEM, V1999, P431, DOI 10.1002/(SICI)1099-0690(199902)1999:2<431::AID-EJOC431>3.0.CO
[13]  
2-I
[14]   From 3,4-dinitrothiophene to 1,2-diaryl-4-nitrobenzenes through (E,E,E)-1,6-diaryl-3-nitro-1,3,5-hexatrienes [J].
Dell'Erba, C ;
Gabellini, A ;
Mugnoli, A ;
Novi, M ;
Petrillo, G ;
Tavani, C .
TETRAHEDRON, 2001, 57 (43) :9025-9031
[15]   Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks [J].
Dell'Erba, C ;
Gabellini, A ;
Novi, M ;
Petrillo, G ;
Tavani, C ;
Cosimelli, B ;
Spinelli, D .
TETRAHEDRON, 2001, 57 (38) :8159-8165
[16]  
Dell'Erba C, 2000, EUR J ORG CHEM, V2000, P903
[17]   RING-OPENING REACTION IN THIOPHEN SERIES - REAACTION BETWEEN 3,4-DINITROTHIOPHEN AND SECONDARY AMINES [J].
DELLERBA, C ;
SPINELLI, D ;
LEANDRI, G .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (10) :549-&
[18]   Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene. Access to 1,4-disubstituted 2,3-dinitro-1,3-butadienes and 2,3-diaminobutanes [J].
DellErba, C ;
Novi, M ;
Petrillo, G ;
Spinelli, D ;
Tavani, C .
TETRAHEDRON, 1996, 52 (09) :3313-3326
[19]   BASE-INDUCED CYCLOADDITION OF TOSYLMETHYL OR (TERT-BUTOXYCARBONYL)METHYL ISOCYANIDE TO 1,4-DISUBSTITUTED 2,3-DINITRO-1,3-BUTADIENES - ACCESS TO 2,3-DISUBSTITUTED 4-ETHYNYLPYRROLES [J].
DELLERBA, C ;
GIGLIO, A ;
MUGNOLI, A ;
NOVI, M ;
PETRILLO, G ;
STAGNARO, P .
TETRAHEDRON, 1995, 51 (17) :5181-5192
[20]   SYNTHETIC EXPLOITATION OF THE RING-OPENING OF 3-4-DINITROTHIOPHENE .4. SYNTHESIS OF 1,4-DISUBSTITUTED 3-HYDROXIMINO-2-NITRO-1-BUTENES AND THEIR CYCLIZATION TO 4-NITROISOXAZOLES [J].
DELLERBA, C ;
NOVI, M ;
PETRILLO, G ;
STAGNARO, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (04) :861-865