Synthesis 2025; 57(02): 397-406
paper
Special Topic Dedicated to Prof. H. Ila
A Regioselective Domino Benzannulation Route to Indeno[1,2-a ]fluorene-7,12-diones
Vijaykumar Naik
,
We are grateful to CSIR, and to the Science and Engineering Research Board (SERB), India, for financial support (CRG/2022/004763).
Abstract
A base-promoted domino benzannulation reaction of 2,3-dibromoindenone with acyclic 1,3-dicarbonyls resulted in an efficient synthetic protocol for a series of novel polycyclic indeno[1,2-a]fluorenes. The reaction proceeds via the two sequential addition-elimination reactions of nucleophilic species generated from the 1,3-dicarbonyls under basic conditions, serendipitously leading to the benzannulation with two molecules of 2,3-dibromoindenone. The second addition-elimination occurs on the initially formed adduct of 1,3-dicarbonyl with 2,3-dibromoindenone, setting the stage for further intramolecular cyclization and aromatization. Interestingly, unsymmetrical 1,3-dicarbonyls furnished a single regioisomer. The origin of the regioselectivity and plausible mechanism is discussed.
Key word
2,3-dibromoindenone -
indeno[1,2-a]fluorene -
domino reaction -
benzannulation -
addition-elimination reaction
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2395-5433.
Supporting Information
Publication History
Received: 09 June 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Reference
1
Evdokimov NM,
Van Slambrouck S,
Heffeter P,
Tu L,
Le Calvé B,
Lamoral-Theys D,
Hooten CJ,
Uglinskii PY,
Rogelj S,
Kiss R,
Steelant WF. A,
Berger W,
Yang JJ,
Bologa CG,
Kornienko A,
Magedov IV.
J. Med. Chem. 2011; 54: 2012
2
Anand D,
Yadav PK,
Patel OP. S,
Parmar N,
Maurya RK,
Vishwakarma P,
Raju KS. R,
Taneja I,
Wahajuddin M,
Kar S,
Yadav PP.
J. Med. Chem. 2017; 60: 1041
3
Wu X,
Li X,
Li Z,
Yu Y,
You Q,
Zhang X.
J. Med. Chem. 2018; 61: 11280
4
Tugrak M,
Inci Gul H,
Sakagami H,
Gulcin I,
Supuran CT.
Bioorg. Chem. 2018; 81: 433
5
Beck DE,
Reddy PV. N,
Lv W,
Abdelmalak M,
Tender GS,
Lopez S,
Agama K,
Marchand C,
Pommier Y,
Cushman M.
J. Med. Chem. 2016; 59: 3840
6
Chaudhri N,
Grover N,
Sankar M.
Inorg. Chem. 2018; 57: 11349
7
Dressler JJ,
Zhou Z,
Marshall JL,
Kishi R,
Takamuku S,
Wei Z,
Spisak SN,
Nakano M,
Petrukhina MA,
Haley MM.
Angew. Chem. Int. Ed. 2017; 56: 15363
8
Mishra S,
Fatayer S,
Fernández S,
Kaiser K,
Peña D,
Gross L.
ACS Nano 2022; 16: 3264
9
Huang HH,
Prabhakar C,
Tang KC,
Chou PT,
Huang GJ,
Yang JS.
J. Am. Chem. Soc. 2011; 133: 8028
10
Gómez-Esteban S,
Benito-Hernandez A,
Termine R,
Hennrich G,
Navarrete JT. L,
Ruiz Delgado MC,
Golemme A,
Gómez-Lor B.
Chem. Eur. J. 2018; 24: 3576
11
Sanguinet L,
Williams JC,
Yang Z,
Wieg RJ,
Mao G,
Singer KD,
Wiggers G,
Petschek RG.
Chem. Mater. 2006; 18: 4259
12
Asadi S,
Mohammadi Ziarani G.
Mol. Diversity 2016; 20: 111
13
Sun J,
Liu X,
Sun Q,
Han Y,
Yan C.-G.
J. Org. Chem. 2023; 88: 11562
14
Das S.
New J. Chem. 2020; 44: 17148
15
Das S.
RSC Adv. 2020; 10: 18875
16
Singh R,
Bhardwaj D,
Saini MR.
RSC Adv. 2021; 11: 4760
17
Kachanov AV,
Slabko OY,
Baranova OV,
Shilova EV,
Kaminskii VA.
Tetrahedron Lett. 2004; 45: 4461
18
Bekere L,
Larina N,
Lokshin V,
Ellern A,
Sigalov M,
Khodorkovsky V.
New J. Chem. 2016; 40: 6554
19
Lokshin V,
Bekere L,
Khodorkovsky V.
Dyes Pigm. 2017; 145: 570
20
Sigalov MV,
Shainyan BA,
Chipanina NN,
Oznobikhina LP.
J. Phys. Chem. A 2013; 117: 11346
21
Forren MJ,
Roberts CA,
Allen ST,
Helmy S.
Dyes Pigm. 2021; 194: 109619
22
Batenko N,
Neibolte I,
Belyakov S,
Valters R.
J. Fluoresc. 2016; 26: 23
23
Kurose A,
Ishida Y,
Hirata G,
Nishikata T.
Angew. Chem. Int. Ed. 2021; 60: 10620
24
Bürckstümmer H,
Tulyakova EV,
Deppisch M,
Lenze MR,
Kronenberg NM,
Gsänger M,
Stolte M,
Meerholz K,
Würthner F.
Angew. Chem. Int. Ed. 2011; 50: 11628
25
Kronenberg NM,
Steinmann V,
Bürckstümmer H,
Hwang J,
Hertel D,
Würthner F,
Meerholz K.
Adv. Mater. 2010; 22: 4193
26
Tietze LF,
Brasche G,
Gericke KM.
Domino Reactions in Organic Synthesis 2006
27
Kotha S,
Misra S,
Halder S.
Tetrahedron 2008; 64: 10775
28
Cao J,
Sun J,
Yan C.-G.
Org. Biomol. Chem. 2019; 17: 9008
29
Liu D,
Liu X,
Sun J,
Yan C.-G.
J. Org. Chem. 2021; 86: 14705
30
Liu D,
Liu X,
Sun J,
Han Y,
Yan C.-G.
Org. Biomol. Chem. 2022; 20: 4964
31
Tsukamoto H,
Nomura Y,
Doi T.
Heterocycles 2019; 99: 549
32
Akrawi OA,
Khan A,
Hussain M,
Mohammed HH,
Villinger A,
Langer P.
Tetrahedron Lett. 2013; 54: 3037
33
Basurto S,
García S,
Neo AG,
Torroba T,
Marcos CF,
Miguel D,
Barberá J,
Blanca Ros M,
Rosario De La Fuente M.
Chem. Eur. J. 2005; 11: 5362
34
Hussain M,
Hung NT,
Khera RA,
Villinger A,
Langer P.
Tetrahedron Lett. 2011; 52: 184
35
Raveendra Babu K,
Ahmed Khan F.
Org. Biomol. Chem. 2015; 13: 299
36
Nigam R,
Raveendra Babu K,
Ghosh T,
Kumari B,
Das P,
Anindya R,
Ahmed Khan F.
Chem. Biol. Drug Des. 2021; 97: 1170
37
Negi R,
Jena TK,
Jyoti N,
Tuti NK,
Anindya R,
Khan FA.
Org. Biomol. Chem. 2022; 20: 5820
38
Nigam R,
Babu KR,
Ghosh T,
Kumari B,
Akula D,
Rath SN,
Das P,
Anindya R,
Khan FA.
Bioorg. Med. Chem. 2018; 26: 4100
39
Naik V,
Khan FA.
ARKIVOC 2022; (vi): 66
40
Naik V,
Khan FA.
ARKIVOC 2023; (vii): 202312095
41
Yuting T,
Ziyang C,
Kexin S,
Yongsheng Z.
Adv. Synth. Catal. 2023; 22: 3909
42
Zinad DS,
Hussain M,
Villinger A,
Langer P.
Eur. J. Org. Chem. 2011; 4212
