Zn(OTf)2-Catalyzed 1,6-Conjugate Addition of Benzoxazinones to p-Quinone Methides: Access to 3,3-Diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic Acid Esters

Neha Dua; Sonali Ghosh; Rama Krishna Peddinti

doi:10.1055/s-0040-1706600

Synlett, Table of Contents

Synlett 2021; 32(04): 411-416
DOI: 10.1055/s-0040-1706600

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Zn(OTf)₂-Catalyzed 1,6-Conjugate Addition of Benzoxazinones to p-Quinone Methides: Access to 3,3-Diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic Acid Esters

Neha Dua

^aDepartment of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttrakhand, India

,

Sonali Ghosh

^bSupramolecular and Structural Chemistry Laboratory, School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Argul, Bhubaneswar-752 050, India

,

Rama Krishna Peddinti ∗

^aDepartment of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttrakhand, India

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Abstract

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Abstract

An effective method for the synthesis of 3,3-diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic acid esters is reported. A novel zinc triflate-catalyzed regioselective 1,6-conjugate addition of vinylogous carbamates to p-quinone methides for accessing the title compounds has been developed. This protocol furnished the hybrid compounds in good to excellent yields. The reaction is rapid and has a broad substrate scope.

Key words

para-quinone methides - vinylogous carbamates - 1,6-addition - regioselectivity - diastereoselectivity - benzoxazines

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References

References and Notes
1 Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
2 Brahmachari G. RSC Adv. 2016; 6: 64676
3 Chen Z, Rong M.-Y, Nie J, Zhu X.-F, Shi B.-F, Ma J.-A. Chem. Soc. Rev. 2019; 48: 4921
4 Armaly AM, DePorre YC, Groso EJ, Riehl PS, Schindler CS. Chem. Rev. 2015; 115: 9232
5 Mukherjee S, Yang JW, Hoffman S, List B. Chem. Rev. 2007; 107: 5471

6a Park C.-H, Ryabova V, Seregin IV, Sromek AW, Gevorgyan V. Org. Lett. 2004; 6: 1159
6b Bellina F, Benelli F, Rossi R. J. Org. Chem. 2008; 73: 5529

7 Seregin IV, Ryabova V, Gevorgyan V. J. Am. Chem. Soc. 2007; 129: 7742
8 Yang Y, Chen L, Zhang Z, Zhang Y. Org. Lett. 2011; 13: 1342
9 Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219
10 Gardner PD, Rafsanjani HS, Rand L. J. Am. Chem. Soc. 1959; 81: 3364

11a Decker M. Curr. Med. Chem. 2011; 18: 1464
11b Tietze LF, Bell HP, Chandrasekhar S. Angew. Chem. Int. Ed. 2003; 42: 3996
11c Xu H, Laraia L, Schneider L, Louven K, Strohmann C, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2017; 56: 11232

12a Takao K.-i, Sasaki T, Kozaki T, Yanagisawa Y, Tadano K.-i, Kawashima A, Shinonaga H. Org. Lett. 2001; 3: 4291
12b Martin HJ, Magauer T, Mulzer J. Angew. Chem. Int. Ed. 2010; 49: 5614
12c Jansen R, Gerth K, Steinmetz H, Reinecke S, Kessler W, Kirschning A, Müller R. Chem. Eur. J. 2011; 17: 7739

13a Larsen AA. Nature 1969; 224: 25
13b Hamels D, Dansette PM, Hillard EA, Top S, Vessières A, Herson P, Jaouen G, Mansuy D. Angew. Chem. Int. Ed. 2009; 48: 9124

14 Lima CG. S, Pauli FP, Costa DC. S, de Souza AS, Forezi LS. M, Ferreira VF, da Carvalho da Silva F. Eur. J. Org. Chem. 2020; 2650
15 Schmid TE, Drissi-Amaraoui S, Crévisy C, Baslé O, Mauduit M. Beilstein J. Org. Chem. 2015; 11: 2418
16 Goswami P, Singh G, Anand RV. Org. Lett. 2017; 19: 1982
17 Zhang B, Liu L, Mao S, Zhou M.-D, Wang H, Li L. Eur. J. Org. Chem. 2019; 3898
18 Rathod J, Sharma BM, Mali PS, Kumar P. Synthesis 2017; 49: 5224
19 Shirsath SR, Shinde GH, Shaikh AC, Muthukrishnan M. J. Org. Chem. 2018; 83: 12305

For recent examples, see:

20a Roiser L, Zielke K, Waser M. Synthesis 2018; 50: 4047
20b Zhao S, Zhu Y, Zhang M, Song X, Chang J. Synthesis 2019; 51: 2136
20c Torán R, Vila C, Sanz-Marco A, Muñoz MC, Pedro JR, Blay G. Eur. J. Org. Chem. 2020; 627
20d Winter M, Schütz R, Eitzinger A, Ofial AR, Waser M. Eur. J. Org. Chem. 2020; 3812
20e Ghotekar GS, Shirsath SR, Shaikh AC, Muthukrishnan M. Chem. Commun. 2020; 56: 5022

For selected asymmetric reactions, see:

20f Chu W.-D, Zhang L.-F, Bao X, Zhao X.-H, Zeng C, Du J.-Y, Zhang G.-B, Wang F.-X, Ma X.-Y, Fan C.-A. Angew. Chem. Int. Ed. 2013; 52: 9229
20g Caruana L, Kniep F, Johansen TK, Poulsen PH, Jørgensen KA. J. Am. Chem. Soc. 2014; 136: 15929

21 Li X, Liu N, Zhang H, Knudson SE, Slayden RA, Tonge PJ. Bioorg. Med. Chem. Lett. 2010; 20: 6306
22 Bakthadoss M, Kannan D, Srinivasan J, Vinayagam V. Org. Biomol. Chem. 2015; 13: 2870
23 Lee CL, Chan KP, Lam Y, Lee YS. Tetrahedron Lett. 2001; 42: 1167
24 Böhme TM, Augelli-Szafran CE, Hallak H, Pugsley T, Serpa K, Schwarz RD. J. J. Med. Chem. 2002; 45: 3094 : corrigendum: J. Med. Chem. 2002, 45, 4800
25 Mitscher LA, Sharma PN, Chu DT. W, Shen LL, Pernet AG. J. Med. Chem. 1987; 30: 2283
26 Birch M, Bradley PA, Gill JC, Kerrigan F, Needham PL. J. Med. Chem. 1999; 42: 3342
27 CCDCs 2015516 and 2012570 contain the supplementary crystallographic data for compounds 7 and 16, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
28 3,3-Diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoate Esters 3–21: General Procedure The appropriate benzoxazine 2 (0.5 mmol) was added to a stirred solution of the appropriate p-QM derivative 1 (0.6 mmol) in MeCN (3 mL), and the mixture was stirred at rt. Zn(OTf)₂ (2 mol%) was added, and the mixture was stirred at rt until the reaction was complete (TLC). The crude mixture analyzed by ¹H NMR to determine the dr of the diastereomers, then purified by chromatography on a short column [silica gel (100–200 mesh), EtOAc–hexanes (5:95)]. Methyl 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-(2-oxo-2H-1,4-benzoxazin-3-yl)-3-phenylpropanoate (3) Reaction time: 5 min. White solid; yield: 5 mg (93%); mp 146.4–147.6 °C (mixture of diastereomers). ¹H NMR (400 MHz, CDCl₃): δ = 7.78 (d, J = 8.0 Hz, 1 H), 7.49 (d, J = 8.0 Hz, 2 H), 7.43 (t, J = 8.0 Hz, 2 H), 7.34–7.28 (m, 4 H), 7.23–7.13 (m, 4 H), 7.04 (t, J = 8.0 Hz, 1 H), 6.96 (s, 2 H), 5.29 (d, J = 4.0 Hz, 1 H), 5.25 (d, J = 4.0 Hz, 1 H), 5.07–5.02 (m, 1 H), 4.93 (d, J = 12.0 Hz, 1 H), 4.91 (s, 1 H, OH), 3.56 (s, 3 H), 3.47 (s, 1 H), 1.41 (s, 7 H), 1.21 (s, 18 H). ¹³C NMR (100 MHz, CDCl₃): δ = 170.1, 170.0, 154.2, 152.4, 152.1, 146.1, 142.6, 135.8, 135.7, 131.3, 131.2, 131.1, 129.3, 128.6, 127.8, 125.5, 116.3, 52.6, 34.4, 34.2, 30.4, 30.1. HRMS (ESI-TOF): m/z [M + Na] ⁺ calcd for C₃₂H₃₅NNaO₅: 536.2407; found: 536.2408.

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