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Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one Full article

Journal Russian Journal of Organic Chemistry
ISSN: 1608-3393 , E-ISSN: 1070-4280
Output data Year: 2018, Volume: 54, Number: 4, Pages: 606-613 Pages count : 8 DOI: 10.1134/s1070428018040152
Authors Markosyan A.I. 1 , Hayrapetyan K.K. 1 , Gabrielyan S.H. 1 , Shirinyan V.Z. 2 , Mamyan S.S. 1 , Avakimyan J.A. 1 , Stepanyan G.M. 1
Affiliations
1 Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, Armenia
2 Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

Abstract: The condensation of 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carbonitrile with chloroacetyl chloride afforded chloro-N-(2-cyano-3,3-dimethyl-3,4-dihydronaphthalen-1-yl)acetamide which underwent cyclization to 2-(chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one. The latter reacted with various nucleophiles (alkali metal alkoxides, piperazine, 2-sulfanylethanol) to give 2-(alkoxymethyl)-, 2-(piperazin-1-ylmethyl)-, and 2-{[(2-hydroxyethyl)sulfanyl]methyl}-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin- 4(3H)-ones. The condensation of 2-(chloromethyl)benzo[h]quinazoline with 2-thioxo derivatives of quinazoline and benzo[h]quinazolines led to the formation of bis-quinazolines in which 5,5-dimethyl-5,6- dihydrobenzo[h]quinazolin-4(3H)-one fragment is linked to quinazoline or benzo[h]quinazoline system through a CH2S bridge.
Cite: Markosyan A.I. , Hayrapetyan K.K. , Gabrielyan S.H. , Shirinyan V.Z. , Mamyan S.S. , Avakimyan J.A. , Stepanyan G.M.
Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one
Russian Journal of Organic Chemistry. 2018. V.54. N4. P.606-613. DOI: 10.1134/s1070428018040152 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000434488900015
Scopus: 2-s2.0-85048146285
OpenAlex: W2806437299
Citing:
DB Citing
OpenAlex 10
Scopus 6
Web of science 10
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