Some Transformations of 4′-Amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile

Some Transformations of 4′-Amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2022, Volume: 92, Number: 10, Pages: 1887-1893 Pages count : 7 DOI: 10.1134/s1070363222100024

Authors

Markosyan A.I. ¹ , Ayvazyan A.S. ¹ , Gabrielyan S.A. ¹ , Danghyan M.Yu. ¹ , Shirinyan V.Z. ² , Arsenyan F.H. ¹

Affiliations

1	Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991 Russia

The corresponding Schiff bases were synthesized by condensation of 4′-amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile with anilines. The reaction of the indicated aminonitrile with 4-chlorobutanoyl chloride and subsequent cyclization of the intermediate amide gave rise to 2-(3-chloropropyl)-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one, which in the presence of potassium hydroxide underwent cyclization to form 10,11-dihydro-5H-spiro[benzo[h]pyrrolo[2,1-b]quinazolin-6,1′-cycloheptane]-7(9H)-one. The reaction of the aminonitrile with ethyl-3-chloro-3-oxopropanoate and cyclization of the corresponding intermediate amide furnished ethyl 2-(4-oxo-4,6-dihydro-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-2-yl)acetate. The latter was hydrolyzed to give 2-methyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one, further condensation of which with aromatic aldehydes afforded heterostilbenes possessing antitumor properties.

Markosyan A.I. , Ayvazyan A.S. , Gabrielyan S.A. , Danghyan M.Y. , Shirinyan V.Z. , Arsenyan F.H.
Some Transformations of 4′-Amino-1′H-spiro[cycloheptane-1,2′-naphthalene]-3′-carbonitrile
Russian Journal of General Chemistry. 2022. V.92. N10. P.1887-1893. DOI: 10.1134/s1070363222100024 WOS Scopus OpenAlex

Web of science:	WOS:000882594400002
Scopus:	2-s2.0-85141374583
OpenAlex:	W4308544938

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