Reactions of 1-Amino-5-Morpholino-6,7,8,9-Tetrahydrothieno[2,3-<i>c</i>] Isoquinoline- 2-Carbonitrile

El‐Dean, Adel M. Kamal; Radwan, Shaban M.; Zaki, Remon M.

doi:10.3184/030823410x12868184096970

Cited by 10 publications

(1 citation statement)

References 23 publications

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“…In the light of the prior biological activities of tetrahydroisoquinolines and in resumption of our project for synthesis of new heterocycles containing the thienotetrahydroisoquinolines moiety, − we have announced here preparation of the new 1-amino-2-substituted and 1-pyrrolyl-2-substituted-5-piperidinyl-6,7,8,9-tetrahydrothieno[2,3- c ]isoquinolines and their fused heterocycles which have proved promising antibacterial and antifungal activities parallel to the standard drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

et al. 2019

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A novel series of 1-amino-2-substituted-5- piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a−e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, 1 H NMR, 13 C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

et al. 2019

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ChemInform Abstract: Reactions of 1‐Amino‐5‐morpholino‐6,7,8,9‐tetrahydrothieno [2,3‐c]isoquinoline‐2‐carbonitrile.

2011

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A Convenient Synthetic Method and Spectral Characterization of New Tetrahydro[1,3]oxazinothieno[2,3‐c]isoquinoline and Its Pyrimidine Derivatives

Zaki

Radwan

El‐Dean

2017

J Chinese Chemical Soc

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Acetylation of 1‐amino‐5‐morpholin‐4‐yl‐6,7,8,9‐tetrahydrothieno[2,3‐c]isoquinoline‐2‐phenyl carboxamide 3 afforded the corresponding tetrahydro[1,3]oxazinothieno[2,3‐c]isoquinolinone compound 4. The oxazinone compound 4 underwent nucleophilic substitution reactions with various primary aliphatic and aromatic amines including some sulfa drugs such as sulfanilamide, sulfaguanidine, and sulfathiazole to afford the substituted pyrimidinone compounds 6–10. Chlorination of the pyrimidinone 10 with phosphorus oxychloride yielded the chloropyrimidine derivative 11. The latter compound was used as a versatile precursor for the synthesis of other heterocyclic rings containing the tetrahydropyrimidothienoisoquinoline moiety 12–23 through reaction with a variety of organic reagents. The newly synthesized compounds were fully characterized by elemental and spectral analyses, including melting point, TLC, and FT IR and 1H NMR spectroscopy, as well as 13C NMR and mass spectroscopy for most of them. These molecules should allow to us in the future to investigate their pharmacological activities.

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Reactions of 1-Amino-5-Morpholino-6,7,8,9-Tetrahydrothieno[2,3-c] Isoquinoline- 2-Carbonitrile

Cited by 10 publications

References 23 publications

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

ChemInform Abstract: Reactions of 1‐Amino‐5‐morpholino‐6,7,8,9‐tetrahydrothieno [2,3‐c]isoquinoline‐2‐carbonitrile.

A Convenient Synthetic Method and Spectral Characterization of New Tetrahydro[1,3]oxazinothieno[2,3‐c]isoquinoline and Its Pyrimidine Derivatives

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