Synthesis of Densely Functionalized 3a,4-Dihydro-1H-Pyrrolo[1,2-b]Pyrazoles via Base Mediated Domino Reaction of Vinyl Malononitriles with 1,2-Diaza-1,3-dienes

被引：39
作者：
Attanasi, Orazio A. [1 ]
Favi, Gianfranco [1 ]
Geronikaki, Athina [2 ]
Mantellini, Fabio [1 ]
Moscatelli, Giada [1 ]
Paparisva, Aliki [2 ]
机构：
[1] Univ Urbino Carlo Bo, Sect Organ Chem & Organ Nat Cpds, Dept Biomol Sci, I-61029 Urbino, PU, Italy
[2] Aristotle Univ Thessaloniki, Dept Pharmaceut Chem, Sch Pharm, Thessaloniki 54124, Greece
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 11期
关键词：
CONDENSED RING-SYSTEMS; MICHAEL ADDITION; CASCADE REACTIONS; AZOALKENES;
D O I：
10.1021/ol401336s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A domino reaction of vinyl malononitriles (VMs) with 1,2-diaza-1,3-dienes (DDs) produce unprecedented 3a,4-dihydro-1H-pyrrolo[1,2-b]pyrazole systems in a chemo-, regio-, and stereoselective fashion. This base promoted (DIPEA) one-pot transformation involving multiple steps constructs one new C-C bond, two C-N bonds, and two new fused heterocyclic rings with total atom economy.
引用
收藏
页码：2624 / 2627
页数：4
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  • [1] Powerful Approach to Heterocyclic Skeletal Diversity by Sequential Three-Component Reaction of Amines, Isothiocyanates, and 1,2-Diaza-1,3-dienes
    Attanasi, Orazio A.
    Bartoccini, Silvia
    Favi, Gianfranco
    Giorgi, Gianluca
    Perrulli, Francesca Romana
    Santeusanio, Stefania
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) : 1161 - 1167
  • [2] Divergent Regioselective Synthesis of 2,5,6,7-Tetrahydro-1H-1,4-diazepin-2-ones and 5H-1,4-Benzodiazepines
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Mantellini, Fabio
    Nicolini, Simona
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) : 8320 - 8328
  • [3] Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine-Azoene Annulation
    Attanasi, Orazio A.
    Favi, Gianfranco
    Mantellini, Fabio
    Moscatelli, Giada
    Santeusanio, Stefania
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) : 2860 - 2866
  • [4] Cultivating the Passion to Build Heterocycles from 1,2-Diaza-1,3-dienes: the Force of Imagination
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Filippone, Paolino
    Mantellini, Fabio
    Perrulli, Francesca R.
    Santeusanio, Stefania
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) : 3109 - 3127
  • [5] A novel method for the synthesis of functionalized spirocyclic oxindoles by one-pot tandem reaction of vinyl malononitriles with isatylidene malononitriles
    Babu, Thelagathoti Hari
    Joseph, A. Abragam
    Muralidharan, D.
    Perumal, Paramasivan T.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (06) : 994 - 996
  • [6] BENZIMIDAZOLE CONDENSED RING-SYSTEM .9. POTENTIAL ANTINEOPLASTICS - NEW SYNTHESIS OF SOME PYRIDO[1,2-A]BENZIMIDAZOLES AND RELATED DERIVATIVES
    BADAWEY, E
    KAPPE, T
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (04) : 327 - 332
  • [7] Organocatalytic asymmetric deconjugative Michael additions
    Bell, Mark
    Frisch, Kim
    Anker Jorgensen, Karl
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) : 5407 - 5410
  • [8] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress
    Casiraghi, Giovanni
    Battistini, Lucia
    Curti, Claudio
    Rassu, Gloria
    Zanardi, Franca
    [J]. CHEMICAL REVIEWS, 2011, 111 (05) : 3076 - 3154
  • [9] Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides
    Chen, Jia-Rong
    Dong, Wan-Rong
    Candy, Mathieu
    Pan, Fang-Fang
    Joerres, Manuel
    Bolm, Carsten
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (16) : 6924 - 6927
  • [10] Domino Approach for the Synthesis of Pyrrolo[1,2-a]pyrazine from Vinyl Azides
    Chen, Wenteng
    Hu, Miao
    Wu, Jianwei
    Zou, Hongbin
    Yu, Yongping
    [J]. ORGANIC LETTERS, 2010, 12 (17) : 3863 - 3865
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