Halochrome Molekeln. 7. Mitteilung. Synthese und acidobasisches Verhalten substituierter Heteroarenochinazoline

Abstract

We have synthetized a series of substituted heteroarenoquinazolines. The 90-MHz F T 'H-NMR spectra of starting and final products supported the postulated structures. Fragmentation in the mass spectra also were consistant with the assumed structures. With acid, the compounds partly form ring-opened, intensely coloured triphenylcarbenium salts of the Rhoduline-R type (C.I. 42565). UVjVIS spectra of the salts are discussed on the basis of VEPPP-CI calculations. The cPH. curves in buffered MeOH/H,O solutions and the pK* values are determined. The title compounds undergo very complex protonation equilibria.

Halochrome Moleküle 9. Mitteilung[1]. Substituierte 6,11‐Dihydrospiro[[1]benzopyrano[4,3‐b]indol‐6,9′‐9′H‐xanthen]‐2′,6′‐diamine und ihre Aza‐analogen: Neue Chromogene für schwarze Farbbilder

“…3,461 (q. J = 7,0 [7,1], (CH,CH2),N- (6) H 7,14, N 9,03, 0 10,31; gef. : C 73,51, H 7,27 [1,16] (t, J = 7,O [7,2], (CH,CH2),N-C(2)); 1,24 [1,28] ( t , J = 7,0 [7,0], CH,CH,),N-C (6) H 7,74, N 8,28; gef. : C 74,5, H 7,7, N 8,2. (4).…”

“…89-90". 'H-NMR (CDCI,): 1,20 [1,19] ( t , J = 7.0 [7,2], (CH3CH2),N); 3,44 [3,69] (f, J = 7,0 [7,2] H 6,41, N 5,24,011,97;gef. :C76,7O,H6,45,N5,25,011,95. 3.…”

“…Die Extrakte wurden wie unten angegeben weiterverarbeitet. [1,36] (t, J =7,1 [7,2], CH,CH,NH-C(Z)); 1,24 (1,251 (t, J = 7,0 [7,1], (CH,CH,),N-C(6)); 3,24 [ca. 3,451 (q, J = 7,l [7,2], CH$H,NH-C(Z)); 3.45 [cu.…”

“…Die Chromogene 17-32 sowie das zu Vergleichszwecken benotigte 2,6-Bis(diethylamino)-9-(2-phenylindo1-3-yl)xanthylium-perchlorat (37)') wurden einheitlich nach dem [8,25] 6,94 [7,75] 7,24 [7,40] 6,45 [6,40] 6,68 16,701 8,13 [8,05] 3,O [2,8] [8,25] 7,07 [8,11] 7,28 [7,55] 6,45 [6,52] 6,67 [6,76] 8,14 [8,131 3,l [2,7] 9,o ~9 1 2,4 PSI 9,1 "%11 2 4 7,52 [8,36] 7,15 [7,99] 7,32 [7,54] 6,48 [6,53] 6,72 [6,79] 8,17 [8,141 3,2 [3,0] 9,1 [ 7,31 [7,83] 6,92 [7,51] 7,29 [7,39] 6,31 [6,341 636 [6,601 8,15 [8,111 3,O [2,2] [8,22] 6,98 [7,61] 7,25 [7,33] 6,45 [6,44] 6,62 …”

“…Ein zweites Ziel war die Variation der Substituenten an N-C (2) und N-C(6), ebenfalls rnit der Absicht, das Saure-Base-Verhalten zu verandern, aber auch um Einfluss auf das Absorptionsverhalten im VIS-Bereich zu nehmen.…”