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

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

Publication History

Received: 12 November 2020

Accepted: 08 January 2021

Accepted Manuscript online:
08 January 2021

Article published online:
09 February 2021

• 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