A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines

Dedicated to Prof. Scott Denmark on his birthday.

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65^th birthday

Abstract

During exploration of the nickel(0)-catalyzed reaction of isocyanates and isatoic anhydrides, it was found that changes in the substitution pattern of the isocyanate led to constitutionally isomeric quinazolinediones [quinazoline-2,4(1H,3H)-diones] or benzoxazinone imines [2-imino-1,2-dihydro-4H-3,1-benzoxazin-4-ones]. Ligand and solvent screening experiments allowed for identification of conditions that could lead to each constitutional isomer in good to excellent levels of selectivity and yield. Comprehensive characterization of the previously poorly characterized benzoxazinone imines is also provided.

Key words

quinazolinedione - benzoxazinone - nickel - cycloaddition

• References

• 1a Thakur A. Louie J. Acc. Chem. Res. 2015; 48: 2354
• 1b Kumar P. Louie J. In Transition-Metal-Mediated Aromatic Ring Construction . Tanaka K. Wiley; New York: 2013. Chap. 2, 37
• 1c Saito S. In Modern Organonickel Chemistry . Tamaru Y. Wiley-VCH; Weinheim: 2005. Chap. 6, 171
• 2 Varela JA. Saá C. Chem. Rev. 2003; 103: 3787
• 3 Yamamoto Y. Kinpara K. Saigoku T. Takagishi H. Okuda S. Nishiyama H. Itoh K. J. Am. Chem. Soc. 2005; 127: 605
• 4a Amatore M. Aubert C. Eur. J. Org. Chem. 2015; 265
• 4b Reissig H.-U. Zimmer R. In Science of Synthesis . Vol. 33. Molander G.-A. Thieme; Stuttgart: 2006: 371
• 5a Sun M. Ma Y.-N. Li Y.-M. Tian Q.-P. Yang S.-D. Tetrahedron Lett. 2013; 54: 5091
• 5b Nakai K. Kurahashi T. Matsubara S. Chem. Lett. 2013; 42: 1238
• 5c Yoshino Y. Kurahashi T. Matsubara S. J. Am. Chem. Soc. 2009; 131: 7494
• 6a Gutnov A. Heller B. Fischer H.-J. Drexler A. Spannenberg D. Sundermann C. Sundermann B. Angew. Chem. Int. Ed. 2004; 43: 3795
• 6b Wakatsuki Y. Yamazaki H. Tetrahedron Lett. 1973; 14: 3383
• 7 Hong P. Yamazaki H. Synthesis 1977; 50
• 8 Onodera G. Shimizu Y. Kimura J. Kobayashi J. Ebihara Y. Kondo K. Sakata K. Takeuchi R. J. Am. Chem. Soc. 2012; 134: 10515
• 9 Onodera G. Suto M. Takeuchi R. J. Org. Chem. 2012; 77: 908
• 10 McCormick MM. Duong HA. Zuo G. Louie J. J. Am. Chem. Soc. 2005; 127: 5030
• 11a Duong HA. Cross MJ. Louie J. J. Am. Chem. Soc. 2004; 126: 11438
• 11b Hoberg H. Oster BW. J. Organomet. Chem. 1982; 234: C35
• 12a Duong HA. Louie J. Tetrahedron 2006; 62: 7552
• 12b Hoberg H. Oster BW. J. Organomet. Chem. 1983; 252: 359
• 13 Kashima K. Teraoka K. Uekusa H. Shibata Y. Tanaka K. Org. Lett. 2016; 18: 2170
• 14 Tanaka K. Wada A. Noguchi K. Org. Lett. 2005; 7: 4737
• 15 Kondo T. Nomura M. Ura Y. Wada K. Mitsudo T. Tetrahedron Lett. 2006; 47: 7107
• 16 Yamamoto Y. Okuda S. Itoh K. Chem. Commun. 2001; 1102
• 17 Yamamoto Y. Takagishi H. Itoh K. Org. Lett. 2001; 3: 2117
• 18a Spahn NA. Nguyen MH. Renner J. Lane TK. Louie J. J. Org. Chem. 2017; 82: 234
• 18b Knoch F. Kremer F. Schmidt U. Zenneck U. Le Floch P. Mathey F. Organometallics 1996; 15: 2713
• 19 Watterson SH. De Lucca GV. Shi Q. Langevine CM. Liu Q. Batt DG. Bertrand MB. Gong H. Dai J. Yip S. Li P. Sun D. Wu D.-R. Wang C. Zhang Y. Traeger SC. Pattoli MA. Skala S. Cheng L. Obermeier MT. Vickery R. Discenza LN. D’Arienzo CJ. Zhang Y. Heimrich E. Gillooly KM. Taylor TL. Pulicicchio C. McIntyre KW. Galella MA. Tebben AJ. Muckelbauer JK. Chang C. Rampulla R. Mathur A. Salter-Cid L. Barrish JC. Carter PH. Fura A. Burke JR. Tino JA. J. Med. Chem. 2016; 59: 9173
• 20 Beutner GL. Hsiao Y. Razler T. Simmons EM. Wertjes W. Org. Lett. 2017; 19: 1052
• 21a Wang D.-W. Lin H.-Y. Cao R.-J. Yang S.-G. Chen Q. Hao G.-F. Yang W.-C. Yang G.-F. J. Agric. Food. Chem. 2014; 62: 11786
• 21b Kakuta H. Tanatani A. Nagasawa K. Hashimoto Y. Chem. Pharm. Bull. 2003; 51: 1273
• 21c Kakuta H. Koiso Y. Nagasawa K. Hashimoto Y. Bioorg. Med. Chem. Lett. 2003; 13: 83
• 22a Buettner G. Klauke E. Kaspers H. Ferohberger PE. DE 2218302, 1973
• 22b Wagner G. Rothe L. Pharmazie 1971; 26: 725
• 22c Hegarty AF. Bruice TL. J. Am. Chem. Soc. 1970; 92: 6575
• 22d Sheehan JC. Daves DG. J. Org. Chem. 1964; 29: 3599
• 22e Herlinger H. Angew. Chem. Int. Ed. 1964; 3: 378
• 22f Doleschall G. Lempert K. Tetrahedron Lett. 1963; 4: 1195
• 22g Lempert K. Doleschall G. Tetrahedron Lett. 1963; 4: 781
• 22h Anders B. Kuehle E. BE 632578, 1963
• 23 CCDC 1541563 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 24 Bantreil X. Bourderioux A. Mateo P. Hagerman CE. Selkti M. Brachet E. Belmont P. Org. Lett. 2016; 18: 4814
• 25 See Supporting Information for full ligand/solvent screening results
• 26 Dierkes P. van Leeuwen PW. N. M. J. Chem. Soc., Dalton Trans. 1999; 1519
• 27 Uhlig E. Maaser M. Z. Anorg. Allg. Chem. 1966; 344: 205
• 28 Wuestenberg B. Pflatz A. Adv. Synth. Catal. 2008; 350: 174
• 29 Kurihara M. Yoda N. Bull. Chem. Soc. Jpn. 1966; 39: 1942
• 30 Goertz W. Keim W. Vogt D. Englert U. Boele MD. K. van der Veen LA. Kamer PC. J. van Leeuwen PW. N. M. J. Chem. Soc., Dalton Trans. 1998; 2981
• 31 Kurihara M. Yoda N. Tetrahedron Lett. 1965; 6: 2597
• 32 Schulenberg JW. Archer S. Org. React. 1965; 14: 1
• 33 Guan W. Sakaki S. Kurahashi T. Matsubara S. Organometallics 2013; 32: 7564