NMR Studies on Imidines. I. An ¹H and ¹³C NMR study of 10,12‐dihydroisoindolo[1,2‐b]quinazoline‐12‐one

Abstract

ABSTRACT.10,I2-Dihydroisoindolo[1.2-b]qui~zoline-l2-one (2) waa prepared and fully examined by IH and I3C NMR spectroscopy in CDC13 and DMSO-d6 solution.

Novel and Mild Route to Phthalocyanines and 3‐Iminoisoindolin‐1‐ones via N,N‐Diethylhydroxylamine‐Promoted Conversion of Phthalonitriles and a Dramatic Solvent‐Dependence of the Reaction

“…of Et 2 NOH to Pn; although the latter species are unstable, they were detected in ESI + -MS. If the reaction is performed in CDCl 3 or purified CHCl 3 , both 22 and 23 are subject to further transformations (Route D) to furnish 3-imi- noisoindolin-1-ones 18 and the known [21] In the case of 23, its conversion proceeds via the amino tautomer of isoindolinone, which then undergoes the known tautomerization [22] to the more stable imino form 18. The double addition of a nucleophile at a single cyano group is very rare [11,23] but it has been ascertained in our previous study [11] on the conversion of phthalonitriles into phthalocyanines mediated by an oxime (also an HON nucleophile).…”

“…In the case of 23, its conversion proceeds via the amino tautomer of isoindolinone, which then undergoes the known tautomerization [22] to the more stable imino form 18. The double addition of a nucleophile at a single cyano group is very rare [11,23] but it has been ascertained in our previous study [11] on the conversion of phthalonitriles into phthalocyanines mediated by an oxime (also an HON nucleophile).…”

A Green One-Pot Synthesis of vic-Amidino (Hetero)aromatic Acids from 1,2-Dinitriles

“…Free bases are unstable: an attempted transformation of ester hydrochlorides 22a,b into bases on treatment with NaHCO 3 or Et 3 N in MeOH immediately led to intramolecular cyclization to 3-amino-1H-isoindol-1-one (4, Scheme 8) that had been synthesized earlier from 2-cyanobenzamide in 80% yield. 19 The tautomeric structure of 4 has been proven by Xray diffraction.…”

“…IR (KBr), cm -1 : 3338, 3069, 1686, 1615, 1579, 1522, 1466, 1432, 1377. 1 H NMR (400 MHz, D 2 O, 25 ºС): δ = 3.33 (s, 3H, CH 3 OH), 3.89 (s, 3Н, OСH 3 ), 7.25 (d, J = 8.4 Hz, 1H, H Ar ), 7.36 (d, J = 8.0 Hz, 1H, H Ar ), 7.58 (dd, J 1 = 8.0 Hz, J 2 = 8.4 Hz, 1H, H 5 ). 13 To freshly prepared solution of MeONa obtained by dissolving sodium metal (0.035 g, 1.5 mmol) in MeOH (7 mL) quinoxaline-2,3-dicarbonitrile 15 (0.270 g, 1.5 mmol) was added.…”