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NMR spectra of product mixture from reaction of 7 with 1e.

N 3 - Alkylation during formation of quinazolin-4-ones from condensation of anthranilamides and ortho amides

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NMR spectra of product mixture from reaction of 7 with 1e.

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  1. N3-Alkylation during formation of quinazolin-4-ones from condensation of anthranilamides and orthoamides Amit Nathubhai, Richard Patterson, Timothy J. Woodman, Harriet E. C. Sharp, Miranda T. Y. Chui, Hugo H. K. Chung, Stephanie W. S. Lau, Jun Zheng, Matthew D. Lloyd, Andrew S. Thompson and Michael D. Threadgill Medicinal Chemistry, Department of Pharmacy & Pharmacology, University of Bath, Claverton Down, Bath BA2 7AY, UK ELECTRONICSUPPLEMENTARY INFORMATION NMR spectra of product mixture from reaction of 7 with 1e. NMR spectra of product mixture from reaction of 9 with 1e. NMR spectra of product mixture from reaction of 10 with 1e. NMR spectra of isolated compounds. NMR spectra of mixture of quinazolin-4-ones formed by reaction of 7 with 1g. 30 39 48 2 56

  2. 1H NMR spectrum of 8. 13C NMR spectrum of 8.

  3. 1H NMR spectrum of 9. 13C NMR spectrum of 9.

  4. 1H NMR spectrum of 10. 13C NMR spectrum of 10.

  5. 1H NMR spectrum of 11. 13C NMR spectrum of 11.

  6. 1H NMR spectrum of 12. 13C NMR spectrum of 12.

  7. 1H NMR spectrum of 26a. 13C NMR spectrum of 26a.

  8. 1H NMR spectrum of 26b. 13C NMR spectrum of 26b.

  9. 1H NMR spectrum of 26c. 13C NMR spectrum of 26c.

  10. 1H NMR spectrum of 26d. 13C NMR spectrum of 26d.

  11. 1H NMR spectrum of 26f. 13C NMR spectrum of 26f.

  12. 1H-1H NOESY spectrum of 26f. HMBC spectrum of 26f.

  13. 1H NMR spectrum of 27a. 13C NMR spectrum of 27a.

  14. 1H NMR spectrum of 27b. 13C NMR spectrum of 27b.

  15. 1H NMR spectrum of 27c. 13C NMR spectrum of 27c.

  16. 1H NMR spectrum of 27d. 13C NMR spectrum of 27d.

  17. Part of 1H NMR spectrum of 27e. Part of 1H NMR spectrum of 27e. Part of 1H NMR spectrum of 27e.

  18. 1H NMR spectrum of 28a. 13C NMR spectrum of 28a.

  19. 1H NMR spectrum of 28b. 13C NMR spectrum of 28b.

  20. 1H NMR spectrum of 28c. 13C NMR spectrum of 28c.

  21. 1H NMR spectrum of 28d. 13C NMR spectrum of 28d.

  22. 1H NMR spectrum of 29a. 13C NMR spectrum of 29a.

  23. 1H NMR spectrum of 29b. 13C NMR spectrum of 29b.

  24. 1H NMR spectrum of 29c. 13C NMR spectrum of 29c.

  25. 1H NMR spectrum of 30a. 13C NMR spectrum of 30a.

  26. 1H NMR spectrum of 30b. 13C NMR spectrum of 30b.

  27. 1H NMR spectrum of 31a. 13C NMR spectrum of 31a.

  28. 1H NMR spectrum of 32b. 13C NMR spectrum of 32b.

  29. 1H NMR spectrum of crude 47f. 13C NMR spectrum of crude 47f.

  30. 1H NMR spectrum of mixture of quinazolines formed by reaction of 7 with 1e. Part of 1H NMR spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26a 47e 26e

  31. Parts of 1H NMR spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 47e 26e 13C NMR spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 47e 26e

  32. 1H-1H COSY spectrum of mixture of quinazolines formed by reaction of 7 with 1e. Part of 1H-1H COSY spectrum of mixture of quinazolines formed by reaction of 7 with 1e.

  33. Part of 1H-1H COSY spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 47e 26e 26e/47e HSQC spectrum of mixture of quinazolines formed by reaction of 3a with 1e. 19a 26a 26e/47e 26a 47e 26e 26e/47e 26a 26e 47e

  34. Part of HSQC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26a 26e 47e 26a 26e/47e 47a HMBC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26e 26a

  35. Part of HMBC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 47e 26a 26e 47e 47e Part of HMBC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26a 26e 26a 26a

  36. Part of HMBC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26a 26e 26a Part of HMBC spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26a 26e/47e 26e/47e 26e/47e

  37. 1H-1H NOESY spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26e 47e 26a 26e/47e 26a 26e/47e 26e 47e 26a 26e 26a Part of 1H-1H NOESY spectrum of mixture of quinazolines formed by reaction of 7 with 1e. 26e 47e 26e 26e/47e 26a 26e

  38. 1H NOE difference spectrum (irradiation at d 1.5) of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26e 47e 26e/47e 1H NOE difference spectrum (irradiation at d 5.58) of mixture of quinazolines formed by reaction of 7 with 1e. 47e 26e/47e 1H NOE difference spectrum (irradiation at d 5.00) of mixture of quinazolines formed by reaction of 7 with 1e. 26e 26e 26e/47e

  39. 1H NMR spectrum of mixture of quinazolines formed by reaction of 9 with 1e. Part of 1H NMR spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 6c 5c 16c 15c 16c 16c

  40. Part of 1H NMR spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28e 13C NMR spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28e

  41. HSQC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 1H-1H COSY spectrum of mixture of quinazolines formed by reaction of 9 with 1e.

  42. Part ofHSQC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28e 28s 21a Part of HSQC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 28a 28e/49e 49e 28e 28e/49e 28a 28e 49a

  43. HMBC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. Part of HMBC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28a 21a 49e 49e 28e 49e 49e

  44. Part of HMBC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 28e 28a Part of HMBC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28e 28a 21a 49e 49e 28a 28e

  45. Part of HMBC spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 28e 28a 28e/49e 28e/49e 28e 49e 1H-1H NOESY spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 21a 49e 28e 28a 28e/49e 28a 28e

  46. Part of 1H-1H NOESY spectrum of mixture of quinazolines formed by reaction of 9 with 1e. 28a 28e 49e 49e 28e 28e/49e 28a 28e 49e

  47. 1H NOE difference spectrum (irradiation at d 1.5) of mixture of quinazolines formed by reaction of 9 with 1e. 28e 28e 49e 28e/49e 1H NOE difference spectrum (irradiation at d 4.99) of mixture of quinazolines formed by reaction of 9 with 1e. 28e 28e 28e/49e 1H NOE difference spectrum (irradiation at d 5.56) of mixture of quinazolines formed by reaction of 9 with 1e. 49e 28e/49e

  48. 1H NMR spectrum of mixture of quinazolines formed by reaction of 10 with 1e. Part of 1H NMR spectrum of mixture of quinazolines formed by reaction of 10 with 1e. 29a 50e 29e 22a 50e

  49. Parts of 1H NMR spectrum of mixture of quinazolines formed by reaction of 10 with 1e. 50e 29e 13C NMR spectrum of mixture of quinazolines formed by reaction of 10 with 1e.

  50. Parts of 13C NMR spectrum of mixture of quinazolines formed by reaction of 10 with 1e.

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