Adv Synth Catal - 2018 - Verma - Synthesis of Indenopyridine Derivatives Via MgI2 Promoted 2 4 Cycloaddition Reaction of

FULL PAPER DOI: 10.1002/adsc.
201800598
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2
3
4
Synthesis of Indenopyridine Derivatives via MgI2-Promoted
5 [2 + 4] Cycloaddition Reaction of In-situ Generated 2-
6
7
Styrylmalonate from Donor-Acceptor Cyclopropanes and
8 Chalconimines
9
10
11 Kamal Vermaa and Prabal Banerjeea,*
12 a
Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab, India Pin 140001
13
Fax: (+ 91)-1881-223395
14
E-mail: prabal@iitrpr.ac
15
16
Received: May 7, 2018; Revised: July 3, 2018; Published online: July 25, 2018
17
18
19
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.201800598
20
21 Abstract: An unexpected MgI2-promoted [2 + 4] cycloaddition reaction of in-situ generated 2-styrylmalonate
22 from donor-acceptor cyclopropanes with chalconimines to synthesize highly substituted indenopyridine
23 derivatives under the mild reaction conditions have been developed. Additionally, these derivatives were
24 utilized for the synthesis of highly substituted 9-membered lactam by oxidative C=C bond cleavage and spiro
25 [oxoindane-pyrrolidine] derivative via Meinwald type rearrangement.
26
27 Keywords: 2-styrylmalonate; donor-acceptor cyclopropanes; indenopyridine; chalconimines
28
29
30 Introduction The ring-opening cycloaddition reaction of donor-
31 acceptor cyclopropanes (DACs) has emerged as a
32 Indenopyridine skeleton is present in a wide range of powerful, effective and atom-economic synthetic tool
33 bioactive natural products and also in pharmaceutical for the construction of cyclic and acyclic compounds.[4]
34 drugs.[1,2,3] Typical examples, such as NSC314622, MJ- In general, the 1,3-zwitterionic nature of DACs makes
35 III-65, indotecan and indimitecan consist of this it to undergo [3 + n] cycloaddition reactions with
36 structural motif shows potential for cancer treatment numerous reactive partners. This type of reactivity of
37 (Figure 1).[1] In addition, hexahydroindenopyridine DACs is most commonly depicted in the literature.
38 structure displayed antidepressant activity,[2] and ony- Melnikov et al. isolated 2-styrylmalonate via the
39 chine exhibited antimicrobial activity.[3] Therefore, the isomerization of 1,3-zwitterion species generated from
40 development of highly efficient methods for the syn- DACs, into the corresponding styrene through positive
41 thesis of these scaffolds from readily available starting charge shift.[5a]
42 materials has received significant attention. Most commonly, in-situ generated 2-styrylmalonate
43 from DACs are involved in cyclopropanes dimeriza-
44 tion.[5] However, limited [2 + n] cycloadditions have
45 been reported in the literature where cyclopropane
46 diesters were used as a source of 2-styrylmalonates. In
47 2014, Wang et al. reported AlCl3-promoted formal
48 [2 + 3]-cycloaddition of DACs with N-benzylic sulpho-
49 namides where DACs serves as a source of 2-
50 styrylmalonate.[6] Recently, Tomilov and his co-worker
51 reported cycloaddition of 2-styrylmalonate, an alter-
52 native of DAC, with aldehydes, to afford dihydropyr-
53
Figure 1. Selected examples with indenopyridine scaffold.
anones.[7] (Scheme 1)
54 Azadienes contain two conjugated p-bonds and
55 commonly involved in [4 + n] cycloaddition reac-
56 tions.[8] Previously, Zhong et al. reported phosphine-
57 catalyzed [4 + 2] annulation reaction of azadienes with
Adv. Synth. Catal. 2018, 360, 3687 – 3692 3687 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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FULL PAPER asc.wiley-vch.de
1 (1-azadiene, oxathianes, thiazines, etc.).[11,13] Based on

2 previous experiences, we started the cycloaddition
3 with 10 mol% of MgI2 which furnished 58% yield of
4 3 aa (Table 1, entry 3). Increased dosage of MgI2 up to
5 50 mol% gave almost similar yield (Table 1, entry 4,
6 5). But further increment of MgI2 up to 100 mol%,
7 produced 50% yield of 3 aa, and decomposition of 1 a
8 was observed (Table 1, entry 6). Later, we checked the
9 efficiency of the reaction with other magnesium
10 containing Lewis acids. Magnesium halides, such as
11 chloride and bromide, Mg(OTf)2 were ineffective for
12 the reaction at 20 mol% of catalyst loading at room
13 temperature (See Supporting Information (SI)). A
14 series of indium containing Lewis acids, like InCl3,
15 InI3, In(OTf)3 were also employed, decomposition of
16 DAC 1 a and chalconimine 2 a was observed, leading
17 to a complex mixture (See SI). Relatively weak Lewis
18 acids like FeCl2, ZnI2 and Yb(OTf)3 were found
19 Scheme 1. [2 + n] cycloaddition reactions. ineffective to catalyze the reaction (See SI). Other
20 Lewis acids such as Cu(OTf)2 and Bi(OTf)3 gave 45%
21 and 48% yield, respectively (Table 1, entry 7, 8). The
22 vinyl ketones.[9] In 2017, Namboothiri and his co- reaction proceeds well with solvents such as CH2Cl2,
23 worker described [4 + 1] and [4 + 2] cycloaddition CHCl3, while no reaction was observed in case of
24 reactions of N-ylide with azadienes for the synthesis of tetrahydrofuran and acetonitrile (Table 1, entry 4, 9,
25 fused cyanopyrroles and spirocyclopropanes.[10] To the 10, 11).
26 best of our knowledge, [4 + n] cycloaddition reactions
27 of azadienes with DACs are not reported yet in the
28 literature. We have recently reported a Lewis acid Table 1. Optimization of reaction conditions.[a]
29 catalyzed formal [3 + 2]-cycloaddition of DACs with
30 azadienes, wherein cyclopropanes act as “classical”
31 1,3-zwitterion to afford N-tosyl, or nosyl imine
32 functionalized cyclopentanes and pyrrolidine deriva-
33 tives.[11] Encouraged by these results, we took an
34 interest to explore the reactivity of DACs with
35 chalconimine. Interestingly, [2 + 4] cycloaddition prod- entry LA LA (mol%) solvent time (h) yield (%)[b]
36 uct was obtained. Herein, we report a MgI2-promoted
1 – – CH2Cl2 12 n.r[c]
37 [2 + 4] cycloaddition reaction of DACs; a source of 2-
2 MgI2 5 CH2Cl2 8 n.r[c]
38 styrylmalonate instead of the “classical” 1,3-zwitterion
3 MgI2 10 CH2Cl2 8 58
39 intermediate with chalconimine to synthesize densely 4 MgI2 20 CH2Cl2 5 61
40 functionalized indenopyridine derivatives (Scheme 1). 5 MgI2 50 CH2Cl2 4 60
41 These derivatives were further utilized towards the 6 MgI2 100 CH2Cl2 4 50
42 synthesis of macrocyclic keto-lactams by oxidative C= 7 Bi(OTf)3 20 CH2Cl2 3 45
43 C bond cleavage and spiro[oxoindane-pyrrolidine] 8 Cu(OTf)2 20 CH2Cl2 6 48
44 derivatives via Meinwald type rearrangement. The 9 MgI2 20 CHCl3 14 60
45 scaffold of these derivatives is found in many 10 MgI2 20 CH3CN 16 n.r[c]
46 important bioactive molecules.[12] 11 MgI2 20 THF[d] 16 n.r[c]
47 [a]
All reactions were carried out under inert atmosphere: 1 a
48 (0.10 mmol, 1 equiv.), 2 a (0.10 mmol, 1 equiv.), Lewis acid,
49
Results and Discussion
solvent (1 mL) in rt.
50 Initially, DAC 1 a and chalconimine 2 a were chosen as [b]
Isolated yield after flash column chromatography.
[c]
51 the model substrates to identify and optimize the n.r = no reaction.
[d]
52 reaction parameters such as solvents and Lewis acids. THF = Tetrahydrofuran.
53 The findings are summarized in Table 1. Previously,
54 our group has observed that 10 or 20 mol% of MgI2 is
55 a fruitful catalyst for the ring opening cycloaddition Under the optimized reaction condition, we further
56 reaction of DACs with other strained rings such as evaluated the scope of [2 + 4] cycloaddition reaction
57 epoxides and aziridines and also with other substrates with varieties of DACs (1 a–1 m) and chalconimines
1 (2 a–2 i), containing either relatively electron-poor or substituted DACs furnished the corresponding prod-
2 -rich groups present at the variable position of aryl ucts 3 ga, 3 ia and 3 ha with excellent yields in 1,2-
3 ring and the results are depicted in Table 2 and 3. dichloroethane at 80 8C. Noticeably, phenyl ring con-
4 taining or substituents including methyl, fluoro groups
5 at the para-position of the aromatic ring in DACs gave
6
Table 2. Substrate scope with respect to DACs 1.[a] their corresponding products in 200 mol% loading of
7 MgI2 (see SI for the optimization of the reaction
8 conditions). No product was observed in the case of
9 electron-withdrawing group substituted DAC 1 m
10 having NO2 group present at para-position of the
11 benzene ring. 2,4,6-Trimethylphenyl-substituted DAC
12 (1 l) failed to undergo the reaction in 1,2-dichloro-
13 ethane at 80 8C. The reaction also did not proceed
14 with 2-furly 1 j, and N-benzylindol-3-yl 1 k incorpo-
15 rated DACs, decomposition of cyclopropanes were
16 observed.
17 Next, we investigated the substrate scope with a
18 wide range of chalconimine 2 (Table 3). The yield of
19 the reaction was affected when para position of the N-
20 arylsulfonyl group was incorporated with an electron
21 withdrawing functionality; this may be due to the
22 steric and electronic effects of the group. N-Tosyl 2 a
23 and N-benzenesulfonyl 2 e substituted chalconimine
24 produced the corresponding products 3 ba and 3 be
25 with 62% and 64% yield, respectively. While N-(4-
26 chlorophenyl)sulfonyl 2 f and nosyl 2 g substituted
27 chalconimines gave low yield of the products. p-Tolyl
28 2 b, o-bromophenyl 2 c, p-chlorophenyl 2 d substituted
29 chalconimines produced almost the same yield of the
30 desired products 3 bb, 3 bc, and 3 bd, respectively. In
[a]
31 All reactions were carried out under inert atmosphere: 1 all above cases, we could isolate single isomer other
32 (0.10 mmol, 1.0 equiv.), 2 (0.10 mmol, 1.0 equiv.), MgI2 than the cycloaddition reaction of tetralone derived
33 (0.02 mmol, 0.2 equiv.) at room temperature in CH2Cl2 chalconimine 2 h with DAC 1 b afforded two diaster-
34 (1 mL). eomers 3 bh and 3 bh’ with 72% combined yield. The
[b]
35 Isolated yield after flash column chromatography. configuration of both isomers 3 bh and 3 bh’ were
[c]
36 MgI2 (0.02 mmol, 0.2 equiv.), ClCH2CH2Cl (1 mL) at unambiguously demonstrated by NOE analysis (Fig-
80 8C.
37 [d] ure 2). 2,5-Dibenzylidene cyclopentanone derived
MgI2 (0.25 mmol, 2.0 equiv.), ClCH2CH2Cl (1 mL) at
38 chalconimine 2 i delivered product 3 bi with good yield
80 8C.
39 in 8 h. Therefore, less-activated DACs afforded an
40 excellent yield of the reaction whereas more activated
41 DACs gave moderate yield because of quick decom-
42 Employing more reactive or DACs bearing elec- position of cyclopropanes.
43 tron-donating functionality such as methoxy (1 a, 1 b,
44 1 c, 1 e) and methylenedioxy (1 d) group present at a
45 variable position in vicinal phenyl ring gave 3 aa, 3 ba,
46 3 ca, 3 ea, and 3 da with 60% to 70% yields (Table 2).
47 The constitution and relative configuration of 3 ba was
48 confirmed by single crystal X-ray analysis, and
49 structures of other products were assigned by analogy
50 with compound 3 ba (Table 2, also see the SI).[15]
51 Moreover, an electron-rich DAC 1 f containing Figure 2. NOE observation of products 3 bh and 3 bh’.
52 N,N-dimethyl group at the para position of vicinal
53 phenyl ring gave the product 3 fa under heating at
54 80 8C in 6 h. Significantly, the yield of the reaction was To clarify the reaction mechanism, we have synthe-
55 increased for the DACs bearing less electron-donating sized 2-styrylmalonate according to the reported
56 group in vicinal phenyl ring. Less-activated DACs procedure (Scheme 2).[5a] The reaction of 2-styrylmal-
57 such as p-tolyl 1 g, p-fluorophenyl 1 i, and phenyl 1 h onate 1 a’ and chalconimine 2 a was performed under
1 Table 3. Substrate scope with respect to chalconimines 2.[a] zwitterion intermediate A. It further isomerises to 2-
2 styrylmalonate complex B. This 2-styrylmalonate com-
3 plex B reacts with the chalconimine 2 through hetero-
4 Diels-Alder process[14] which may possibly adopt two
5 transition states (TS), D and E. TS D is more favoured
6 because of secondary orbital interactions in the endo
7 approach which in turn results the formation of
8 compound 3 exclusively. Another possible product, 3’
9 is not observed because of exo-facial approach of E.
10 This phenomenon may also be rationalized with the
11 fact that the steric interaction between Ar1 and
12 methylene group (at C-3 subsituent of chalconi-
13 mine)[14] is greater in exo TS than that of endo TS
14 product. While tetralone derived chalconimine 2 h
15 consists of relatively flexible 6-membered ring, gave
16 two products, endo-facial 3 bh as a major and exo-
17 facial 3 bh’ as minor.
18 The indenopyridine derivative could be applied to
19 some very interesting synthetic transformations. This
20 system contains reactive double bond which could
21 undergo oxidation reactions. Treatment of 3 gg with
22 ruthenium chloride and sodium periodate gave the 9-
23 membered lactam 4 gg by oxidative C=C bond cleav-
[a]
24 All reactions were carried out under inert atmosphere: 1 b age with 75% yields (Scheme 4). Similarly, this reac-
25 (0.10 mmol, 1.0 equiv.), 2 (0.10 mmol, 1.0 equiv.), MgI2 tion with other indenopyridine derivative 3 ia, gave
26 (0.02 mmol, 0.2 equiv.) at room temperature in CH2Cl2 the corresponding 9-membered lactam 4 ia with 80%
27 (1 mL). yield. These type of macrocyclic amine scaffolds show
[b]
28 Isolated yield after flash column chromatography. biological activity against chronic hepatitis B.[12c]
[c]
diastereomeric ratio.
29 The indenopyridine derivatives were further uti-
30 lized for the synthesis of spiro[oxoindane-pyrrolidine]
31 derivative (Scheme 5). The reaction of 3 gg with meta-
32 the optimized conditions. The reaction furnished the chloroperoxybenzoic acid (m-CPBA) at room temper-
33 similar product 3 aa when we replace cyclopropane ature in CH2Cl2 led to the production of spiro
34 with their corresponding styrene. These results suggest [oxoindane-pyrrolidine] derivative 5 gg in 82% yield
35 that in a reaction first cyclopropane was isomerized to via epoxidation followed by Meinwald rearrangement.
36 propene which participates in the reaction. The N-tosyl substituted indenopyridine derivative 3 ga
37 also successfully reacted with m-CPBA providing 5 ga
38 with 83% yield. This spirocyclic structural units found
39 in many potential analgesics.[12a,b] The constitution and
40 relative configuration of 5 gg, 4 ia, and 4 gg were
41 confirmed by single crystal X-ray analysis (Figure 3
42 and also see the SI).[15]
43
44
45
46
47
48
49
50 Scheme 2. [2 + 4] cycloaddition reaction of 2-styrylmalonate
51 1 a’ and chalconimine 2 a for mechanistic study.
52
Figure 3. ORTEP Structures of 5 gg, 4 gg and 4 ia compounds.
53
54
55 On the basis of above result and literature prece-
56 dent[6] (Scheme 3), we assumed that MgI2 activates the
57 DACs 1 and converts it into the opened ring 1,3-
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19 Scheme 3. Plausible mechanism.
20
21
22 Experimental Section
23 Procedure A for 3 aa, 3 ba, 3 ca, 3 da, 3 ea, 3 bb, 3 bc, 3 bd,
24 3 be, 3 bf, 3 bg, 3 bh, 3 bi: A two-necked round bottom flask
25 was charged with donor-acceptor cyclopropane (0.10 mmol,
26 1.0 equiv.), chalconimine (0.10 mmol, 1.0 equiv.) and MgI2
27 (0.02 mmol, 0.2 equiv.) under a nitrogen atmosphere. CH2Cl2
28 (1 mL) was added to the reaction mixture and solution was
29 stirred it at room temperature until the consumption of
Scheme 4. Synthesis of 9-membered lactams.
30 cyclopropane (as monitored by TLC). The reaction mixture
31
was filtered through a thin pad of celite and solvent was
concentrated in a rotary evaporator. The residue was purified
32
by flash column chromatography on silica gel using ethyl
33
acetate/hexane as eluent.
34
35 Procedure B for 3 ga, 3 ha, 3 ia, 3 gg: A two-necked round
36 bottom flask was charged with donor-acceptor cyclopropane
37 (0.10 mmol, 1.0 equiv.), chalconimine (0.10 mmol, 1.0 equiv.)
and MgI2 (0.25 mmol, 2.0 equiv.) under a nitrogen atmos-
38
phere. 1,2-dichloroethane (1 mL) was added to the reaction
39
mixture and solution was stirred it at 80 8C until the
40 Scheme 5. Synthesis of spiro[oxoindane-pyrrolidine] deriva- consumption of cyclopropane (as monitored by TLC). The
41 tives. reaction mixture was filtered through a thin pad of celite and
42 solvent was concentrated in a rotary evaporator. The residue
43 was purified by flash column chromatography on silica gel
44 Conclusion using ethyl acetate/hexane as eluent.
45
46 In conclusions, we have developed a new protocol for
47 the synthesis of indenopyridine derivatives via MgI2- Acknowledgments
48 promoted [2 + 4] cycloaddition reaction of DACs, a KV thanks to the UGC, New Delhi, India for a research
49 source of 2-styrylmalonate with chalconimine. This fellowship. PB acknowledges the DST-India (EMR/2015/
50 derivative was efficiently utilized towards the syn- 002332) and CSIR-India for financial support.
51 thesis of 9-membered lactam and spiro[oxoindane-
52 pyrrolidine] derivatives. Further investigation of bio-
53 logical properties of these heterocyclic compounds is
References
54 currently underway in our laboratory.
[1] a) S. Antony, M. Jayaraman, G. Laco, G. Kohlhagen,
55
K. W. Kohn, M. Cushman, Y. Pommier, Cancer Res.
56
2003, 63, 7428–7435; b) S. Antony, G. Kohlhagen, K.
57
1 Agama, M. Jayaraman, S. Cao, F. A. Durrani, Y. M. kov, Tetrahedron Lett. 2011, 52, 4421–4425; c) R. A.
2 Rustum, M. Cushman, Y. Pommier, Mol. Pharmacol. Novikov, V. A. Korolev, V. P. Timofeev, Y. V. Tomilov,
3 2005, 67, 523–530; c) R. B. Fouce, C. F. Prada, J. M. Tetrahedron Lett. 2011, 52, 4996–4999; d) R. A. Nov-
4 Requena, M. Cushman, Y. Pommier, R. A. Velilla, ikov, D. O. Balakirev, V. P. Timofeev; Y. V. Tomilov,
5 J. M. E. Martnez, E. C. Alvarez, Y. P. Pertejo, R. M. Organometallics 2012, 31, 8627–8638; e) O. A. Ivanova,
Reguera, Antimicrob. Agents Chemother. 2012, 56, E. M. Budynina, D. A. Skvortsov, N. Limoge, A. V.
6
5264–5270; d) D. E. Beck, K. Agama, C. Marchand, A. Bakin, A. O. Chagarovskiy, I. V. Trushkov, M. Y. Melni-
7
Chergui, Y. Pommier, M. Cushman, J. Med. Chem. kov, Chem. Commun. 2013, 49, 11482–11484; f) R. A.
8 2014, 57, 1495–1512. Novikov, A. V. Tarasova, V. A. Korolev, V. P. Timofeev,
9 [2] a) J. Augstein, A. L. Ham, P. R. Leeming, J. Med. Y. V. Tomilov, Angew. Chem. 2014, 126, 3251–3255;
10 Chem. 1972, 15, 466–470; b) R. Kunstmann, U. Lerch, Angew. Chem. Int. Ed. 2014, 53, 3187–3191.
11 H. Gerhards, M. Leven, U. Schacht, J. Med. Chem. [6] M. Zhu, J. Liu, J. Yu, L. Chen, C. Zhang, L. Wang, Org.
12 1984, 27, 432–439; c) R. Kunstmann, G. Fischer, J. Med. Lett. 2014, 16, 1856–1859.
13 Chem. 1984, 27, 1312–1316. [7] D. D. Borisov, R. A. Novikov, A. S. Eltysheva, Y. V.
14 [3] C. D. Hufford, S. Liu, A. M. Clark, B. O. Oguntimein, J. Tkachev, Y. V. Tomilov, Org. Lett. 2017, 19, 3731–3734.
15 Nat. Prod. 1987, 50, 961–964. [8] J. C. M. Monbaliu, K. G. R. Masschelein, C. V. Stevens,
16 [4] Selected review of DACs and recent articles: a) H. -U. Chem. Soc. Rev. 2011, 40, 4708–4739.
17 Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151–1196; [9] Z. Shi, Q. Tong, W. W. Y. Leong, G. Zhong, Chem. Eur.
18
b) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, J. 2012, 18, 9802–9806.
3051–3060; c) M. A. Cavitt, L. H. Phun, S. France,
19 [10] S. P. Midya, E. Gopi. , N. Satam, I. N. N. Namboothiri,
Chem. Soc. Rev. 2014, 43, 804–818; d) T. F. Schneider, J.
20 Org. Biomol. Chem. 2017, 15, 3616–3627.
Kaschel, D. B. Werz, Angew. Chem. 2014, 126, 5608–
21 [11] K. Verma, P. Banerjee, Adv. Synth. Catal. 2017, 359,
5628; Angew. Chem. Int. Ed. 2014, 53, 5504–5523;
22 3848–3854.
e) H. K. Grover, M. R. Emmett, M. A. Kerr, Org.
23 [12] a) P. A. Crooks, H. E. Rosenberg, J. Med. Chem. 1978,
Biomol. Chem. 2015, 13, 655–671; f) A. K. Pandey, A.
24 21, 585–587; b) P. A. Crooks, H. E. Rosenberg, J. Chem.
Ghosh, P. Banerjee, Isr. J. Chem. 2016, 56, 512–521;
25
Soc. Perkin Trans. 1 1979, 2719–2726; c) G. D. Hartman,
g) M. A. Kerr, Isr. J. Chem. 2016, 56, 476–487; h) S.
S. Kuduk, US20160272599 A1, 2016.
26 Racine, J. Vuilleumier, J. Waser, Isr. J. Chem. 2016, 56,
566–577; i) L. Wang, Y. Tang, Isr. J. Chem. 2016, 56, [13] a) A. Ghosh, A. K. Pandey, P. Banerjee, J. Org. Chem.
27
463–475; j) B. Pagenkopf, N. Vemula, Eur. J. Org. 2015, 80, 7235–7242; b) A. K. Pandey, A. Ghosh, P.
28
Chem. 2017, 2017, 2561–2567; k) J. Zhang, H. Jiang, S. Banerjee, Eur. J. Org. Chem. 2015, 11, 2517–2523; c) K.
29 Verma, P. Banerjee, Adv. Synth. Catal. 2016, 358, 2053–
30 Zhu, Adv. Synth. Catal. 2017, 359, 2924–2930; l) L. K. B.
Garve, P. G. Jones, D. B. Werz, Angew. Chem. 2017, 129, 2058; d) A. K. Pandey, R. K. Varshnaya, P. Banerjee,
31 Eur. J. Org. Chem. 2017, 2017, 1647–1656; e) A. Ghosh,
9354–9358; Angew. Chem. Int. Ed. 2017, 56, 9226–9230;
32 S. Mandal, P. K. Chattaraj, P. Banerjee, Org. Lett. 2016,
m) J. Preindl, S. Chakrabarty, J. Waser, Chem. Sci. 2017,
33 18, 4940–4943; f) R. K. Varshnaya, P. Banerjee, Eur. J.
8, 7112–7118; n) R. A. Novikov, A. V. Tarasova, D. A.
34 Denisov, D. D. Borisov, V. A. Korolev, V. P. Timofeev, Org. Chem. 2016, 23, 4059–4066; g) R. Dey, P. Banerjee,
35 Y. V. Tomilov, J. Org. Chem. 2017, 82, 2724–2738; Org. Lett. 2017, 19, 304–307.
36 o) A. U. Augustin, M. Busse, P. G. Jones, D. B. Werz, [14] a) D. L. Boger, W. L. Corbett, T. T. Curran, A. M.
37 Org. Lett. 2018, 20, 820–823. Kasper, J. Am. Chem. Soc. 1991, 113, 1713–1729; b) D.
38 [5] Selected article of 2-styrylmalonate: a) A. O. Chagarov- L Boger, Tetrahedron 1983, 39, 2869–2939.
39 skiy, O. A. Ivanova, E. R. Rakhmankulov, E. M. Budy- [15] CCDC 1586964 (3 ba), CCDC 1810698 (5 gg) and
40 nina, I. V. Trushkov, M. Y. Melnikov, Adv. Synth. Catal. CCDC 1588295 (4 gg) and CCDC 1847562 (4 ia) contain
41 2010, 352, 3179–3184; b) A. O. Chagarovskiy, O. A. the supplementary crystallographic data of this paper.
42 Ivanova, E. M. Budynina, I. V. Trushkov, M. Y. Melni-
43
44
45
46
47
48
49
50
51
52
53
54
55
56
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FULL PAPER DOI: 10.1002/adsc.

1 (1-azadiene, oxathianes, thiazines, etc.).[11,13] Based on

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