Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1-c][1,4]benzoxazines and [1,2,3]Triazolo[5,1-c][1,4]benzoxazepines

Anton V. Budeev; Grigory Kantin; Dmitry Dar’in; Mikhail Krasavin

doi:10.1055/a-1348-9031

Synthesis, Table of Contents

Synthesis 2021; 53(12): 2155-2166
DOI: 10.1055/a-1348-9031

paper

Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1-c][1,4]benzoxazines and [1,2,3]Triazolo[5,1-c][1,4]benzoxazepines

Anton V. Budeev

^aSaint Petersburg State University, Saint Petersburg, 199034, Russian Federation

,

Grigory Kantin

^aSaint Petersburg State University, Saint Petersburg, 199034, Russian Federation

,

Dmitry Dar’in ∗

^aSaint Petersburg State University, Saint Petersburg, 199034, Russian Federation

,

Mikhail Krasavin ∗

^aSaint Petersburg State University, Saint Petersburg, 199034, Russian Federation

^bImmanuel Kant Baltic Federal University, Kaliningrad 236016, Russian Federation

› Author Affiliations

Abstract

All articles of this category

Abstract

Further exploration of the trifunctional character of previously introduced alkyl 4-chloro-2-diazo-3-oxobutanoates in reactions with N-protected substituted o-aminophenols followed by deprotection provided a convenient entry into [1,2,3]triazolo[5,1-c][1,4]benzoxazines, which are of high medicinal importance, as documented in the literature. The same approach applied to N-protected substituted o-(aminomethyl)phenols afforded [1,2,3]triazolo[5,1-c][1,4]benzoxazepines, which are practically unexplored compounds from a medicinal chemistry perspective. The syntheses start with S_N2-type alkylation of the phenol. Removal of the protecting group triggers imine formation followed by Wolff 1,2,3-triazole synthesis.

Key words

diazo compounds - multicenter reactions - nucleophilic substitution - domino reactions - Wolff 1,2,3-triazole synthesis - benzoxazines - benzoxazepines

Full Text

References

References
1 Ganem B. Acc. Chem. Res. 2009; 42: 463
2 Piers E. Pure Appl. Chem. 1988; 60: 107
3 Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis. Wiley-VCH; Weinheim: 2006
4 Posner GH. Chem. Rev. 1986; 86: 831
5 Dar’in D, Khoroshilova O, Kantin G, Krasavin M. Synthesis 2020; 52: 1266
6 Costin TA, Dutra LG, Bortoluzzi AJ, Sá MM. Tetrahedron 2017; 73: 4549
7 Xu J, Wang R. ARKIVOC 2010; (ix): 293
8 Jahani F, Tajbakhsh M, Khaksar S, Azizi M. Monatsh. Chem. 2011; 142: 1035
9 Dubé D, Scholte AA. Tetrahedron Lett. 1999; 40: 2295
10 Hellal M, Singh S, Cuny GD. Tetrahedron 2012; 68: 1674
11 Hu Y, Ma X, Zhang Y, Che Y, Zhao J. ACS Sens. 2016; 1: 22

12a Tsuge O, Ueno K, Inaba A. Heterocycles 1976; 4: 1
12b Fusco R, Garanti L, Zecchi G. J. Org. Chem. 1975; 40: 1906
12c Chowdhury C, Sasmal AK, Dutta PK. Tetrahedron Lett. 2009; 50: 2678
12d Chatterjee N, Sarkar S, Pal R, Sen AK. Tetrahedron Lett. 2014; 55: 2261
12e Suarez JR, Trastoy B, Perez-Ojeda ME, Marin-Barrios R, Chiara JL. Adv. Synth. Catal. 2010; 352: 2515

13 Bromidge SM, Arban R, Bertani B, Bison S, Borriello M, Cavanni P, Dal Forno G, Di-Fabio R, Donati D, Fontana S, Gianotti M, Gordon LJ, Granci E, Leslie CP, Moccia L, Pasquarello A, Sartori I, Sava A, Watson JM, Worby A, Zonzini L, Zucchelli V. J. Med. Chem. 2010; 53: 5827
14 Bertani B, Cremonesi S, Garzya V, Micheli F, Rupcic R, Sabbatini FM. (Glaxo Group Ltd) PCT Int. Appl. WO 2011151361A1, 2011 ; Chem. Abstr. 2011, 156, 1576957.
15 Tomita K, Taoda Y, Iwaki T, Kawasuji T, Akiyama T, Sugiyama S, Tamura Y, Iwatsu M. (Shionogi & Co. Ltd) PCT Int. Appl. WO 2014119636A1, 2014 ; Chem. Abstr. 2014, 161, 1283081.
16 Kubo K, Tobisu M, Honda E, Taniguchi T, Fukase Y, Kawamura M, Nakayama M. (Takeda Pharmaceutical Company Limited) PCT Int. Appl. WO 2006109846A1, 2006 ; Chem. Abstr. 2006, 145, 1096947.

17a Padwa A, Ku A, Ku H, Mazzu A. J. Org. Chem. 1978; 43: 66
17b Orlek BS, Sammes PG, Weller DJ. Tetrahedron 1993; 49: 8179
17c Orlek BS, Sammes PG, Weller DJ. J. Chem. Soc., Chem. Commun. 1993; 607
17d Chandrasekhar S, Seenaiah M, Kumar A, Reddy CR, Mimidyala SK, Kumar CG, Balasubramanian S. Tetrahedron Lett. 2011; 52: 806

18 Illuminati G, Mandolini L, Masci B. J. Am. Chem. Soc. 1975; 97: 4960
19 Best D, Kujawa S, Lam HW. J. Am. Chem. Soc. 2012; 134: 18193
20 Tena Pérez V, Fuentes de Arriba ÁL, Monleón LM, Simón L, Rubio OH, Sanz F, Morán JR. Eur. J. Org. Chem. 2014; 3242
21 Bodero O, Spivey AC. Synlett 2017; 28: 471
22 Sarkar A, Roy SR, Parikh N, Chakraborti AK. J. Org. Chem. 2011; 76: 7132
23 Naro Y, Thomas M, Stephens MD, Connelly CM, Deiters A. Bioorg. Med. Chem. Lett. 2015; 25: 4793
24 Woods M, Sherry AD. Inorg. Chem. 2003; 42: 4401

Supplementary Material

Supporting Information