Subscribe to RSS
Download PDF
DOI: 10.1055/s-2004-834860
2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines
Publication History
Publication Date:
29 September 2004 (online)
Abstract
The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-b]quinazoline-6-carbonitriles in the presence of Et3N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed.
Key words
pyrimidines - cyclizations - nucleophilic aromatic substitutions - quinazolines - acylations
- 1a
Kusar M.Svete J.Stanovnik B. J. Heterocycl. Chem. 1996, 33: 1041 - 1b
Schwartz A.Pal Z.Szabo L.Simon K.Hermecz I.Meszaros Z. J. Heterocycl. Chem. 1987, 24: 645 - 1c
Resnyanskaya EV.Tverdokhlebov AV.Volovenko YuM.Shishkin OV.Zubatyuk RI. Synthesis 2002, 2717 - 1d
Elgemeie GH.Metwally NH. Monatsh. Chem. 2000, 131: 779 - 1e
Ulomskii EN.Deev SL.Rusinov VL.Chupakhin ON. Russ. J. Org. Chem. 1999, 35: 1355 - 1f
Volovenko YuM.Ivanov VV. Chem. Heterocycl. Compd. (N. Y.) 1998, 33: 1124 - 1g
Babu VNSR.Babu AN.Anand V.Hanumanthu P. Synth. Commun. 1998, 28: 4439 - 2a
Babichev FS.Patratii VK.Volovenko YuM.Prodanchuk NG.Sinchenko VG.Nemazani OG.Silaeva TA. Farm. Zh. 1988, 6: 65; Chem. Abstr. 1988, 110, 170097 - 2b
Volovenko YuM.Nemazanyi AG.Ryabokon IG.Babichev FS. Ukr. Khim. Zh. 1988, 54: 295 ; Chem. Abstr. 1988, 110, 38921 - 2c
Volovenko YuM.Nemazanyi AG.Vesel’skaya GL.Tyukhtenko SI.Babichev FS. Dopov. Akad. Nauk Ukr. RSR, Ser. B 1986, 29 ; Chem. Abstr. 1986, 107, 96644 - 2d
Nemazanyi A.Heider N. J. Heterocycl. Chem. 1996, 33: 1147 - 2e
Volovenko YuM.Nemazanyi AG.Vesel’skaya GL.Babichev FS. Dopov. Akad. Nauk Ukr. RSR, Ser. B 1986, 35 ; Chem. Abstr. 1986, 106, 176303 - 2f
Volovenko YuM,Babichev FS,Nemazanyi AG, andShevchenko VA. inventors; SU 1237667. ; Chem. Abstr. 1986, 105, 190977 - 3
Volovenko YuM.Blyumin EV. Tetrahedron 2000, 56: 5185 - 4
Blyumin EV.Volovenko YuM.Neunhoeffer H.Shishkina SV.Zubatyuk RA.Shishkin OV. Tetrahedron 2002, 58: 5733 - 5
Undheim K.Benneche T. In Comprehensive Heterocyclic Chemistry II Vol. 6:Boulton AJ. Elsevier; Oxford: 1996. p.93MissingFormLabel - 6a
Volovenko YuM.Blyumin EV.Schokol TV.Dubinina GG.Babichev FS. Chem. Heterocycl. Compd. (N. Y.) 1997, 33: 445 - 6b
Volovenko YuM.Blyumin EV. Chem. Heterocycl. Compd. (N. Y.) 1998, 34: 324 - 7
Shakhidoyatov HM. Quinazolones-4 and their biological activity Fan; Tashkent: 1998.MissingFormLabel - 8
Volovenko YuM.Blyumin EV. Chem. Heterocycl. Compd. (N. Y.) 1999, 34: 1442 - 9
Burgi H.-B.Dunitz JD. In Structure Correlation Vol. 2: VCH; Weinheim: 1994.MissingFormLabel - 10
Zefirov YV.Zorky PM. Usp. Khim. 1995, 64: 446 - 11
Volovenko YuM.Fursiy TA.Nemazaniy AG.Babichev FS. Dopov. Akad. Nauk Ukr. RSR, Ser. B. 1988, 32 ; Chem. Abstr. 1989, 111, 39301 - 12a
Volovenko YuM.Khilya OV.Volovnenko TA.Shokol TV. Chem. Heterocycl. Compd. (N. Y.) 2002, 38: 314 - 12b
Abdel Aziz MA.Daboun HA.Abdel Gawad SM. J. Prakt. Chem. 1990, 332: 610 - 13
Sheldrick GM. SHELX97. PC Version. A system of computer programs for the determination of crystal structure from X-ray diffraction data. University Göttingen; Germany: 1997.MissingFormLabel
References
Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].