2006
DOI: 10.3390/11070498
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Synthesis of Some Thienopyrimidine Derivatives

Abstract: Thioxothienopyrimidinones, alkylthio-and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolopyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.

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Cited by 37 publications
(29 citation statements)
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“…The reaction of cyclohexanone with ethyl cyanoacetate produced ethyl 2‐amino‐4,5,6,7‐tetrahydrobenzothiophene‐3‐carboxylate ( 9 ) which was further cyclized with formamide to afford the thieno[2,3‐ d ]pyrimidin‐4(3 H )‐one intermediate ( 10 ) . The latter was chlorinated using phosphorous oxychloride to produce 4‐chloro derivative which was used directly in the next reaction due to its high reactivity.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The reaction of cyclohexanone with ethyl cyanoacetate produced ethyl 2‐amino‐4,5,6,7‐tetrahydrobenzothiophene‐3‐carboxylate ( 9 ) which was further cyclized with formamide to afford the thieno[2,3‐ d ]pyrimidin‐4(3 H )‐one intermediate ( 10 ) . The latter was chlorinated using phosphorous oxychloride to produce 4‐chloro derivative which was used directly in the next reaction due to its high reactivity.…”
Section: Resultsmentioning
confidence: 99%
“…Similarly, Gewald procedure was applied using cyclohexanone, malononitrile, sulphur powder, and piperidine in water bath to synthesize the 4,5,6,7-tetrahydrobenzothiophene precursor (6) which was reacted in the same manner with DMF-DMA and then cyclized with intermediates 2a-h to yield the target compounds 8a-h (Scheme 3). The reaction of cyclohexanone with ethyl cyanoacetate produced ethyl 2-amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate (9) [20] which was further cyclized with formamide to afford the thieno [2,3-d] [23]. The latter was chlorinated using phosphorous oxychloride to produce 4-chloro derivative which was used directly in the next reaction due to its high reactivity.…”
Section: Chemistrymentioning
confidence: 99%
“…On the other hand, compounds 7 and 8 could be obtained following different reaction pathways via the procedure reported by El-Baih et al [26]. Thus, 7 could be obtained when the thiourea derivative 5 was heated under reflux in ethanolic sodium hydroxide giving the sodium salt 10 which gave 7 upon acidification with hydrochloric acid (Scheme 4).…”
Section: Resultsmentioning
confidence: 99%
“…Investigation of these two transformations are carried out as per the reported method using cyclohexanone and α-tetralone analogous. 10,11 The results reveals the corresponding carbonitrile functional group contains the expected Michael product.…”
Section: Figure 1 Ortep For Compound 5bmentioning
confidence: 93%