Cycloaddition reactions of phosphorylated 1,2-diaza-1,3-butadienes with olefins:: Regioselective synthesis of pyridazine derivatives

被引：37
|
作者：
Palacios, F [1 ]
Aparicio, D [1 ]
López, Y [1 ]
Santos, JMD [1 ]
Alonso, C [1 ]
机构：
[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Vitoria 01080, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 06期
关键词：
cycloadditions; diazabutadienes; hydrazones; fused-ring systems; nitrogen heterocycles;
D O I：
10.1002/ejoc.200400675
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The aza-Diels-Alder reaction of 4-phosphinyl- and 4-phosphonyl-1,2-diaza-1,3-butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported. Monocyclic, bicyclic and polycyclic tetrahydropyridazines containing a phosphane oxide or a phosphonate substituent are obtained. The formation of cycloadducts can be explained by an endo transition state in the cycloaddition process of these heterodienes with styrene, cyclopentadiene, dihydrofuran, and by means of an exo transition state in the case of norbornadiene. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheirn, Germany, 2005).
引用
收藏
页码：1142 / 1147
页数：6
相关论文
共 50 条
  • [21] SYNTHESIS AND REGIOSELECTIVE [4+2] CYCLOADDITION NUCLEOPHILIC REACTIONS OF N-ARYLAMINO-1,3-DIAZA-1,3-BUTADIENES WITH KETENES AND ACCOMPANYING REARRANGEMENTS
    DEY, PD
    SHARMA, AK
    RAI, SN
    MAHAJAN, MP
    TETRAHEDRON, 1995, 51 (27) : 7459 - 7468
  • [22] SYNTHESIS OF FUNCTIONALLY SUBSTITUTED 1,3-DIAZA-1,3-BUTADIENES
    MAZUMDAR, SN
    MAHAJAN, MP
    SYNTHESIS-STUTTGART, 1990, (05): : 417 - 419
  • [23] 1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience
    Attanasi, OA
    De Crescentini, L
    Filippone, P
    Mantellini, F
    Santeusanio, S
    ARKIVOC, 2002, : 274 - 292
  • [24] Convenient access to new 2-selenazolin-4-one and 2-selenazoline derivatives from 1,2-diaza-1,3-butadienes
    Attanasi, OA
    Filippone, P
    Guidi, B
    Perrulli, FR
    Santeusanio, S
    SYNLETT, 2001, (01) : 144 - 146
  • [25] Azo-coupling decarboxylation reaction of α-carboxy ketene dithioacetals in water -: A new route to 1,2-diaza-1,3-butadienes
    Xu Xian-Xiu
    Wang Mang
    Liu Qun
    Pan Ling
    Zhao Yu-Long
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) : 1431 - 1434
  • [26] Regioselective [4+2] cycloaddition versus nucleophilic reactions of N-arylamino substituted 1,3-diaza-1,3-butadienes with ketenes: Synthesis of pyrimidinone and fused pyrimidinone derivatives .2.
    Dey, PD
    Sharma, AK
    Bharatam, PV
    Mahajan, MP
    TETRAHEDRON, 1997, 53 (40) : 13829 - 13840
  • [27] Sequential construction of complex pyrrole-pyrrole or pyrrole-pyrazole systems from 1,2-diaza-1,3-butadienes
    Attanasi, OA
    De Crescentini, L
    Filippone, P
    Guidi, B
    Perrulli, FR
    Santeusanio, S
    SYNLETT, 1999, (09) : 1367 - 1370
  • [28] Different behavior of the reaction between 1,2-diaza-1,3-butadienes and 1,2-diamines under solvent or solvent-free conditions
    Attanasi, OA
    De Crescentini, L
    Favi, G
    Filippone, P
    Lillini, S
    Mantellini, F
    Santeusanio, S
    SYNLETT, 2005, (09) : 1474 - 1476
  • [29] Cycloaddition of a 1,2-diaza-1,3-butadiene to phenylpropiolic acid: an efficient route to pyridazinoquinolone derivatives
    Padhy, AK
    Purohit, P
    Bardhan, M
    Panda, CS
    Ishar, MPS
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8423 - 8425
  • [30] Chiral heterosubstituted 1,3-butadienes:: Synthesis and [4+2] cycloaddition reactions
    Barluenga, J
    Suárez-Sobrino, A
    Lopez, LA
    ALDRICHIMICA ACTA, 1999, 32 (01) : 4 - 15
12345