Die Synthese von 2,3,4,5‐1H‐Tetrahydroimidazo[2,1‐b]chinazolin‐2,5‐dionen und analogen 2,3,4,5‐1H‐Tetrahydroimidazo[1,2‐a]thieno[2,3‐d] (bzw. [3,2‐d])‐pyrimidin‐2,5‐dionen

Kienzle, Frank; Kaiser, A.; Minder, Rudolf E.

doi:10.1002/hlca.19830660116

Cited by 46 publications

(14 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Then the remainder was collected by filtration and recrystallized from isopropyl alcohol to give 0.91 g (63%) of compound 2, mp 114-115°(ref. [20] A mixture of compound 1 (1.5 g, 7.8 mmol) in methanol (20 ml) and sodium methoxide (0.18 g, 7.8 mmol of sodium dissolved in 6 ml of methanol) was refluxed for 15 min. The solvent was evaporated in vacuo and the resultant salt was dried perfectly.…”

Section: Methyl (2-methylsulfanyl-4-oxo-3(4h)-quinazolinyl)acetate (2)mentioning

confidence: 99%

“…The structure of ester 2 was determined from spectral data. The ir spectra of ester 2 gave two absorption peaks arising from C=O stretching at 1744 (ester) and 1673 cm -1 (lactam [20], however it was obtained using another synthetic sequence. These mentioned data support the structure of compound 2, i.e., N (3) -alkylation.…”

mentioning

confidence: 97%

“…4(3H)-Quinazolinone N (3) -alkanoic acid derivatives exhibit antiinflammatory, antitumor [12], analgetic [13], antihistaminic [14], fungicidal or plant growth regulator properties [15,16]. The most common synthetic methods to N (3) -alkyl 4-oxo-2-mercaptoquinazolines are based on cyclocondensation reactions of anthranilic acid or its derivatives with isothiocyanates [17][18][19], glycinates [20,21] or thiophosgene [22].…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and intramolecular cyclization of 2‐methylsulfany‐4‐oxo‐3(4H)‐quinazolinyl)acetohydrazide

Burbuliene

Bobrovas

Vainilavicius

2006

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Treatment of ambident sodium salt of 2-methylsulfanyl-4(3H)-quinazolinone with methyl bromoacetate resulted in N (3) -alkyl ester formation. Reaction of the resulted ester with hydrazine hydrate gave 2-methylsulfanyl-4-oxo-3(4H)-quinazolinyl)acetohydrazide, which underwent intramolecular cyclization under heating in dimethylformamide to give 1-aminoimidazo[2,1-b]quinazoline-2,5(1H,3H)-dione. The latter took place in acylation reaction and in condensation with aromatic aldehydes.

show abstract

Section: Methyl (2-methylsulfanyl-4-oxo-3(4h)-quinazolinyl)acetate (2)mentioning

confidence: 99%

mentioning

confidence: 97%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and intramolecular cyclization of 2‐methylsulfany‐4‐oxo‐3(4H)‐quinazolinyl)acetohydrazide

Burbuliene

Bobrovas

Vainilavicius

2006

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…In fact, some imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones have been used as gastric secretion inhibitors. 8 However, there are only few reports on the synthesis of imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones.…”

Section: Introductionmentioning

confidence: 99%

New efficient synthesis of imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones via a consecutive aza-Wittig/heterocumulene-mediated annulation

Xie¹,

Huang²,

Ding³

2009

Arkivoc

View full text Add to dashboard Cite

The carbodiimide 2, obtained from aza-Wittig reaction of iminophosphorane 1 with aromatic isocyanate, reacted with α-amino ester in the presence of triethylamine to give imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones 5 (when R 2 is H) or quinazolinones 6 (when R 2 is not H).Imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones 5 were prepared more generally by another route, using a consecutive aza-Wittig / heterocumulene-mediated annulation of iminophosphoranes 9 with isocyanates and catalytic sodium ethoxide.

show abstract

“…The reaction of the isothiocyanate 1 [10] in dichloromethane at room temperature with an ammonium hydroxide solution, with propylamine or methoxycarbonylhydrazine gave the derivatives 2, 5, and 7, respectively.…”

mentioning

confidence: 99%

Synthesis of new thienotriazolopyrimidine and thienopyrimidotetrazine derivatives from bifunctional intermediates

Modica

Santagati

2001

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

New compounds containing the thienotriazolopyrimidine and thienopyrimidotetrazine skeleton are prepared from the bifunctional intermediates 2,3-diamino-5,6-dimethylthieno [2,3-d]pyrimidin-4(3H)-one derivatives 13-17. The 2,pyrimidin-4(1H)-one derivatives 8-12 are also prepared.J. Heterocyclic Chem., 38, 973 (2001).For a long time, our research group has been interested in the synthesis of heterocyclic condensed derivatives, with the aim of evaluating their pharmacological activity, such as analgesic, anti-inflammatory [1-6] and anti-convulsive [7].In recent works, we described the preparation of 3-amino-2-thioxothieno[2,3-d]pyrimidinone [1,8] and of 3-amino-2-phenylaminothieno[2,3-d]pyrimidinone derivatives [7] which are versatile intermediates of bridgehead nitrogen polyheterocycles for the presence of two adjacent reactive functional groups. Through these intermediates, we obtained thiazolothienopyrimidines, thienopyrimidothiadiazoles, thienopyrimidothiadiazines, thienopyrimidotetrazines and thienotriazolopyrimidines [1][2][3][4][5][6][7][8][9].In this work, we report the synthesis of new N3-substituted-2-thioxothieno The reaction of the isothiocyanate 1 [10] in dichloromethane at room temperature with an ammonium hydroxide solution, with propylamine or methoxycarbonylhydrazine gave the derivatives 2, 5, and 7, respectively.The 2-thioxo derivatives 8-11 were obtained from compounds 2, 4 [11], 5, and 7, respectively, by refluxing in an ethanolic potassium hydroxide solution, followed by acidification of the aqueous suspension of the separated solids. Compounds 8 and 11 are identical with those obtained by other synthetic routes [12,13]. Compound 12 was obtained from the isothiocyanate 1 with ethylenediamine under the same experimental conditions adopted for the synthesis of derivatives 2, 5, and 7. By reaction of compounds 2 and 3 [13] with hydrazine hydrate were prepared the 2,3-diamino derivative 13 and the 2-methylamino derivative 15, respectively. The 2-amino-3-methylamino derivative 14 was 973

show abstract

Die Synthese von 2,3,4,5‐1H‐Tetrahydroimidazo[2,1‐b]chinazolin‐2,5‐dionen und analogen 2,3,4,5‐1H‐Tetrahydroimidazo[1,2‐a]thieno[2,3‐d] (bzw. [3,2‐d])‐pyrimidin‐2,5‐dionen

Cited by 46 publications

References 7 publications

Synthesis and intramolecular cyclization of 2‐methylsulfany‐4‐oxo‐3(4H)‐quinazolinyl)acetohydrazide

Synthesis and intramolecular cyclization of 2‐methylsulfany‐4‐oxo‐3(4H)‐quinazolinyl)acetohydrazide

New efficient synthesis of imidazo[2,1-b]quinazoline-2,5(1H,3H)-diones via a consecutive aza-Wittig/heterocumulene-mediated annulation

Synthesis of new thienotriazolopyrimidine and thienopyrimidotetrazine derivatives from bifunctional intermediates

Contact Info

Product

Resources

About