Journal of Heterocyclic Chemistry, ( ISI ), Volume (54), No (1), Year (2017-1) , Pages (151-154)

Title : ( Synthesis of New Derivatives of 4-(4,7,7-Trimethyl-7,8-dihydro-6H-benzo [b]pyrimido[5,4-e][1,4]thiazin-2-yl)morpholine )

Authors: azam karimian , Hossein Eshghi , Mehdi Bakavoli , Ali Shiri ,

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Cyclocondensation of 5-amino-6-methyl-2-morpholinopyrimidine-4-thiol (1) and 2-bromo-5,5-dimethylcyclohexane-1,3-dione (2) under mild reaction condition afforded 4,7,7-trimethyl-2-morpholino-7,8-dihydro-5H-benzo[b]pyrimido[5,4-e][1,4]thiazin-9(6H)-one (3). The 1H and 13C NMR data of compound (3) are demonstrated that this compound exists primarily in the enamino ketone form. Reaction of compound (3) with phosphorous oxychloride gave 4-(9-chloro-4,7,7-trimethyl-7,8-dihydro-6H-benzo[b]pyrimido[5,4-e][1,4]thiazin-2-yl)morpholine (4). Nucleophilic substitution of chlorine atom of compound (4) with typical secondary amines in DMF and K2CO3 furnished the new substituted derivatives of 4-(4,7,7-trimethyl-7,8-dihydro-6H-benzo[b]pyrimido[5,4-e][1,4]thiazin-2-yl)morpholine (5a-h). All the synthesized products were characterized and confirmed by their spectroscopic and microanalytical data.

Keywords

, Heterocyclization, Pyrimidine, Cyclocondensation,
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@article{paperid:1052970,
author = {Karimian, Azam and Eshghi, Hossein and Bakavoli, Mehdi and Shiri, Ali},
title = {Synthesis of New Derivatives of 4-(4,7,7-Trimethyl-7,8-dihydro-6H-benzo [b]pyrimido[5,4-e][1,4]thiazin-2-yl)morpholine},
journal = {Journal of Heterocyclic Chemistry},
year = {2017},
volume = {54},
number = {1},
month = {January},
issn = {0022-152X},
pages = {151--154},
numpages = {3},
keywords = {Heterocyclization; Pyrimidine; Cyclocondensation; Pyrimidothiazine},
}

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%0 Journal Article
%T Synthesis of New Derivatives of 4-(4,7,7-Trimethyl-7,8-dihydro-6H-benzo [b]pyrimido[5,4-e][1,4]thiazin-2-yl)morpholine
%A Karimian, Azam
%A Eshghi, Hossein
%A Bakavoli, Mehdi
%A Shiri, Ali
%J Journal of Heterocyclic Chemistry
%@ 0022-152X
%D 2017

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