ChemInform Abstract: ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES. PART XIII. N‐(3‐QUINAZOLINIO)AMIDATES, IV

Fetter, J.; Lempert, K.; Barta‐Szalai, Gizella; Moeller, J.; Parkanyi, L.

doi:10.1002/chin.197806083

Cited by 3 publications

(7 citation statements)

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“…(EtOH) 222 (4.40)sh, 242 (4.57), 322 (3,82)sh, and 332 (3.85); the U.V. spectrum is in good agreement with the spectra of a series of (9.7), 231 (77), 218 (15), 215 (16), 204 (33), 203 (95), 189 (9.5),187 (5.0), 163 (lo), 147 (18), and 104 (15). (b) In butylamine.…”

Section: Irradiation Of N-(67-dimethoxy-2-methylquinazolin-3-io)-n-[e...supporting

confidence: 67%

“…int.) 292 ( M + ' , 44), 291 (8.8), 277 (13), 259 (18), 203 (M -SH-C4H8,* 39), and 147 (9.2)], and 0-ethyl thiocarbamate [138 mg, 27%; identical (i.r., 'H n.m.r.) with an authentic sample 17].…”

Section: Irradiation Of N-(67-dimethoxy-2-methylquinazolin-3-io)-n-[e...mentioning

confidence: 99%

“…The mixture was evaporated to dryness, and the residue was taken up in dichloromethane (4 ml) to give 6,7-dimethoxy-2-methylquinazoline-4(3H)-thione (14a) [identical (m.p., i.r., mass spectroscopy) with an authentic sample 6] as an insoluble crystalline residue. The dichloromethane solution was extracted with aqueous NaOH and the organic (A) and aqueous layers "1; 2-(2-acetylamino-4,5-dimethoxyphenyll)-5-( 3,4-dimethoxyphenyl)-1, 3,4thidiazole (21bJ[12.5-85 (20), 191 (6.3), 181 (9.9), 177 (8.5), 175 (7.8), 165 (18), 163 (CgHgNO2,t 46), 148 (15), 136 (9.0), 134 (6.0), and 120 (9.9); and 6,7-dimethoxy-2methylquinazolin-4(3H)-one (22a) C8.848.5 mg, 3.5-17.6%; * identical (m-p., i.r.) with an authentic sample"]; a further compound of unknown structure, m.p.…”

Section: Photolysis Of 2-(34-dimethoxyphenyl)-89-dimethoxy-5-mentioning

confidence: 99%

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Electron deficient heteroaromatic ammonioamidates. Part 26. N-(quinazolin-3-io)amidates. Part 13. Phototransformations of an N-(quinazolin-3-io)thioamidate and of a 10bH-1,3,4-thiadiazolo[3,2-c]quinazoline, the ring isomer of an N-(quinazolin-3-io)thioamidate, and the photochemical formation of some 4,4′-biquinazolinyls

Lempert‐Sreter¹,

Lempert²,

Møller³

1984

J. Chem. Soc., Perkin Trans. 1

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Section: Irradiation Of N-(67-dimethoxy-2-methylquinazolin-3-io)-n-[e...supporting

confidence: 67%

Section: Irradiation Of N-(67-dimethoxy-2-methylquinazolin-3-io)-n-[e...mentioning

confidence: 99%

Section: Photolysis Of 2-(34-dimethoxyphenyl)-89-dimethoxy-5-mentioning

confidence: 99%

See 1 more Smart Citation

Electron deficient heteroaromatic ammonioamidates. Part 26. N-(quinazolin-3-io)amidates. Part 13. Phototransformations of an N-(quinazolin-3-io)thioamidate and of a 10bH-1,3,4-thiadiazolo[3,2-c]quinazoline, the ring isomer of an N-(quinazolin-3-io)thioamidate, and the photochemical formation of some 4,4′-biquinazolinyls

Lempert‐Sreter¹,

Lempert²,

Møller³

1984

J. Chem. Soc., Perkin Trans. 1

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“…145-146 "C (from benzene-light petroleum) [Found: C, 58.2; H, 6.7; N, 12.3. C1,H2,N305 ( M , 349.37) requires C, 58.44; H, 6.63; N, 12.03%]; 6 1.25 (s, But), 1.28 (t) and 4.18 (q) (C02Et), 2.12 (s, 2-Me), 5.83 (s, OCH20), 6.24 (s), 6.37 (s), and 6.56 (s) (5, 6-, and 9-H), and 6.7 (bs, NH); m/z (140 "C) (% rel. int.)…”

Section: -Benzoylimino--( 2-methyl-67-methy/enedioxyquinazo/in-mentioning

confidence: 99%

“…1.358 (5) 1.489 (7) 1.318( 5) 1.368( 5) 1.41 8( 6) 1.392( 5) 1.396( 5) 1.408( 6) 1.518( 5) 1.361( 5) 1.370( 5) 1.378 (6) 1.372( 7 1.378( 5) 1.429 (5) 1.436 (7) 1.483( 5) 1.469( 5) 1.400(4) 1.3 5 1 ( 6) 1.284( 6) 1.402( 5) 1.479( 6) 1.363 (7) 1.192(6) 1.331( 6)…”

Section: Elucidation Of the Structures Of The New Photoproducts-unclassified

Electron deficient heteroaromatic ammonioamidates. Part 24. N-(Quinazolin-3-io)amidates. Part 11. The photochemistry of N-(6,7-methylenedioxyquinazolin-3-io)amidates in acetone

Barta‐Szalai¹,

Fetter²,

Lempert³

et al. 1983

J. Chem. Soc., Perkin Trans. 1

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N-(Quinazolin-3-io)amidates (1) may exist, depending on the nature of the groups R, R1, and R2, and in the absence of nucleophiles, as equilibrium mixtures of the monomeric (1) and dimeric (3) forms. For the first time evidence has been found for the generation of photoproducts of the dimeric forms (3) via irradiation of the quinazolinioamidates (1 a-c) in acetone in which substantial amounts of the dimers (3a-c) are present. Thus, the quinazolinioamidates (1 ) are the only heteroaromatic ammonioamidates which are known not only to exist in three forms, viz. the monomer, the adducts (2), and the dimers ( 3 ) , but also to furnish characteristic photoproducts of all three forms.Of the electron deficient heteroaromatic N-ammonioamidates studied so far the N-(quinazolin-3-io)amidates (1) are the only ones which (to a greater or lesser degree, depending on the nature of the ligands R, R1, and R2, as well as the Nu group) are able to form adducts (2) with nucleophiles HNu and, in the absence of such nucleophiles, dimers (3), 4-8 As a consequence, the photochemistry of compounds (1) is more complicated than that of other ammonioamidates. In the presence of nucleophiles (e.g. alcohols,6 toluene-a-thiol,' amines,8 and acetamide *) two series of characteristic photoproducts, originating from forms (1) and (2), respectively, are formed.Here we report the photochemistry of a series of N-(quinazolin-3-io)amidates (la-h) 5 in acetone; this solvent, in the absence of acidic and basic catalysts,' is unable to form type (2) adducts, viz. (1 3), with the amidates. Compounds (la-h) were irradiated in acetone under argon with a highpressure mercury immersion lamp (HPK-125) through Pyrex. Chromatographic work-up of the resulting mixtures furnished the photoproducts (4)-(13) ( Table l).T The majority of the photoproducts had been obtained previously on irradiation of compounds (la-h) in the presence of nucleophiles as shown in Table 2. On the other hand, compounds (9h), (1 1 a-c), and (1 2e) are novel and such products have not been obtained before on irradiation of heteroaromatic ammonioamidates. Compounds (7d) and (7h) are also new. (For proof of the structures of the new compounds, see below.) t For a review on the chemistry of N-(quinazolin-3-io)amidates and related compounds with special emphasis on their photochemistry (see ref. 3). $ Compounds of this type are correctly named as ' amidides '; they are so named in the Experimental section.3 Compounds ( l a -c ) exist in the crystalline state as the pure dimer (3a) and as mixtures of the momers (lb), (lc) and the dimers (3b), (3c), respectively. However, in CDC13 solution equilibria between the monomeric and dimeric forms are rapidly e~tablished.~ This has been shown to be the case for the amidate (1 b), and may be assumed for the amidates (la) and (ic) in solvent acetone as well. It is, thus, immaterial whether monomers or dimers are actually introduced as the starting materials in the (a)-(c) series. 7 Although irradiation was continued until no unchanged starting compounds we...

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Chemistry of Aminimides

Wawzonek¹

1980

Ind. Eng. Chem. Prod. Res. Dev.

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The period 1972-1979 saw considerable activity in research of the chemistry and utilization of aminimides. Studies have extended investigation to aminimides in which the acyl group is derived from imino acids, cyanuric acid, phosphonic acids, and picric acid and to vinylogues of aminimides. Work continued with aminimides derived from nitrogen heterocycles and their conversion to diazepines and bridged nitrogen bicyclic compounds. Commercial utilization of aminimides based on 1,1dimethylhydrazine has been hampered in this country by the loss of the sole commercial source of this compound.

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ChemInform Abstract: ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES. PART XIII. N‐(3‐QUINAZOLINIO)AMIDATES, IV

Cited by 3 publications

References 0 publications

Electron deficient heteroaromatic ammonioamidates. Part 24. N-(Quinazolin-3-io)amidates. Part 11. The photochemistry of N-(6,7-methylenedioxyquinazolin-3-io)amidates in acetone

Chemistry of Aminimides

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