Directed ortho and remote Metalation - Cross coupling connections. Buchwald-Hartwig synthesis of 2-carbamoyl diarylamines. Regioselective anionic routes to acridones, oxindoles, dibenzo-[b,f]azepinones, and anthranilate esters

Synlett

Volumn , Issue 4, 1998, Pages 419-421

  MacNeil, Stephen L ^a   Gray, Matthew ^a,c   Briggs, Laura E ^a   Li, Jim J ^b   Snieckus, V ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b PFIZER INC   (United States)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002294239     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1654     Document Type: Article

References (40)

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13. 2O: C, 76.09; H, 7.51; N, 10.44. Found: C, 76.08; H, 7.43; N, 10.70.
14. Compare with the corresponding Friedel-Crafts method (32% yield, see ref 7).
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29. Metalation of 7a under these conditions for 60 min followed by electrophile quench afforded 2-TMS (58-77%), 2-Me (59%), and 2-PhCH(OH) (48%) N-t-Boc diphenylamines.
30. 8b may be a useful intermediate for acridones related to Glaxo France pharmaceutical GF120918. See Dodic, N.; Dumaitre, B.; Daugan, A.; Pianetti, P. J. Med. Chem. 1995, 38, 2418.
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33. For analogous formation of dibenzooxepinone, dibenzophosphorinone, and dibenzothiepinone systems, see refs. 4 and 5, and footnote 11 in ref. 4, respectively.
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37. All new compounds show analytical and spectral (IR, NMR, MS) data in full agreement with the depicted structures.
38. 3) δ 8.51 (dd, J = 8.0, 1.5 Hz, 1H), 7.70-7.63 (m, 1H), 7.45 (d, J = 8.7 Hz, 1H), 7.27 - 7.21 (m, 1H), 3.81 (s, 3H).
39. Maskiewicz, R.; Sogah, D.; Bruice, T.C. J. Am. Chem. Soc. 1979, 101, 5355.
40. We are grateful to NSERC Canada and Monsanto/Searle for support of our synthetic programs under the Industrial Research Chair award. S. MacNeil is an NSERC Postgraduate Scholar. Professors Steve Buchwald and John Hartwig and their students graciously provided experimental details of their diarylamine synthesis and valuable advice. VS thanks the Dipartimento di Chimica, University of Pisa and Professors P. Salvadori and D. Pino for a Visiting Professorship and cultural hospitality during the preparation of this paper.