NaSH in the construction of thiophene ring fused with N-heterocycles: A rapid and inexpensive synthesis of novel small molecules as potential inducers of apoptosis

Kolli, Sunder Kumar; Nakhi, Ali; Medishetti, Raghavender; Yellanki, Swapna; Kulkarni, Pushkar; Ravikumar, Raju; Pal, Manojit

doi:10.1016/j.bmcl.2014.07.096

Cited by 17 publications

(6 citation statements)

References 18 publications

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“…A further 5-endo-dig-type cyclization results in the formation of the 2-phosphonylated 5-oxopyrimidines 9a-c. The formation of the 3-phosphonylated 5-oxopyrimidines 8a-c is due to the implementation of the usual favorable direction with the attack of chloroethynylphosphonate by the sulfur atom [33,[42][43][44][45][46].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

Kaskevich¹,

Babushkina²,

Gurzhiy³

et al. 2020

Beilstein J. Org. Chem.

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A series of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines was synthesized for the first time by the reactions of chloroethynylphosphonates with unsubstituted and 5(6)-substituted 2-thiouracils. The reaction of chloroethynylphosphonates with 6-substituted 2-thiouracils bearing electron-donor groups (CH3, Ph) proceeded with high regioselectivity involving the cyclization through the N3-nitrogen atom to form new 3-phosphonylated thiazolo[3,2-a]-5-oxopyrimidines with good yield. In the case of unsubstituted and 5-methyl-2-thiouracils, cyclization occurred predominantly through the N1 atom and partially via the N3-nitrogen atom to form a mixture of the corresponding thiazolo[3,2-a]-7- and 5-oxopyrimidines. A dramatic change in the reaction regioselectivity was observed in the case of 6-trifluoromethyl-2-thiouracil that afforded 2- and 3-phosphonylated 5-oxothiazolopyrimidines in a 1:1 ratio.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

Kaskevich¹,

Babushkina²,

Gurzhiy³

et al. 2020

Beilstein J. Org. Chem.

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“…Finally, the pyrrolo[3,2-e]thieno [2,3-b]pyrazines 13a,b were prepared by using the methodology developed in the effort described above. Accordingly, palladium catalysed reactions of 3a,b and phenyl acetylene followed by intramolecular cyclization 26 gives 13a,b in moderate yields (Scheme 3).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Regioselective synthesis of dipyrrolopyrazine (DPP) derivatives via metal free and metal catalyzed amination and investigation of their optical and thermal properties

et al. 2017

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“…2,3-Disubstitued thieno [2,3-b]quinoxaline can be synthesized via the condensation of 2-aminoaniline with thiophene-2,3-dione derivatives [10]. More recently, these derivatives were obtained by the action of NaSH on 3-alkynyl-2-chloroquinoxalines [11]. To date, there is no simple and general method for the synthesis of 2,3-disubstitued thieno [2,3-b]quinoxaline starting from simple chemicals.…”

Section: Introductionmentioning

confidence: 99%

Cyclisation reaction between 3-methylquinoxaline-2-thione and benzaldehydes into 3-benzyl-2-aryl-thieno[2,3-b]quinoxaline promoted by Brønsted acids

Saoudi

Téniou

Debache

et al. 2015

Comptes Rendus. Chimie

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International audience2,3-Disubstituted thieno[2,3-b]quinoxaline derivatives have been synthetized through the condensation of commercially available benzaldehydes with 3-methylquinoxaline-2-thione in EtOH using Brønsted acids, namely sulfuric or hydrochloric acids. A wide range of substituted benzaldehydes has been used, allowing the formation of 3-(substituted)benzyl-2-arylthieno[2,3-b]quinoxalines in high yields in only one ste

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NaSH in the construction of thiophene ring fused with N-heterocycles: A rapid and inexpensive synthesis of novel small molecules as potential inducers of apoptosis

Cited by 17 publications

References 18 publications

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

Regioselective synthesis of dipyrrolopyrazine (DPP) derivatives via metal free and metal catalyzed amination and investigation of their optical and thermal properties

Cyclisation reaction between 3-methylquinoxaline-2-thione and benzaldehydes into 3-benzyl-2-aryl-thieno[2,3-b]quinoxaline promoted by Brønsted acids

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