A synthesis of quinazolines, perimidines and dibenzo[d,f][1,3]diazepines is described. The method involves rearrangements following cyclisation of 2-anilino-2-methoxy-3-oxo-N-phenylbutanethioamides with aromatic 1,3-and 1,4-diamines.
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Compound 5a with formula C22H19N3OS crystallises in the monoclinic system, space group P21/a, with unit cell parameters a = 794.48(3), b = 1439.97(5), c = 1639.56(5) pm, β = 93.217(2)°, V = 1872.8(1) 106 pm3, Z = 4. A total of 2774 independent reflections (R(int) = 0.098) were collected on a sample of size 0.35 × 0.20 × 0.15 mm using Kappa CCD diffractometer and MoKα radiation. The structure was solved by direct methods with SHELXS9713 and refined by the full-matrix least-squares method on F2 using SHELXL9714 program. Final discrepancy indices for 1884 reflections with I>2σ(I) were equal R1 = 0.055, wR2 = 0.105 and R1 = 0.094, wR2 = 0.123 for all 2774 data. The final difference Fourier map of electron density was featureless with the largest peak and hole of 0.27 and −0.23·10−6 e·pm−3, respectively. All calculations and molecular graphics were done using the WinGX package.15 The structural data were deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk) under reference number CCDC 623593.
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