Solid phase synthesis of 1-alkyl-2-alkylthio-5-carbamoylbenzimidazoles

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 201-204

  Lee, Jung ^a   Gauthier, Diane ^a   Rivero, Ralph A ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ALKYL 2 ALKYLTHIO 5 CARBAMOYLBENZIMIDAZOLE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS;

EID: 0032518765     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10525-1     Document Type: Article

References (16)

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13. 7. The cyclization was attempted with thiophosgene, triphosgene, and thiocarbonyldiimidazole using a variety of reaction conditions. Only the reaction with thiocarbonyldiimidazole in THF resulted in a satisfactory cyclization.
14. +).
15. +). NOE was observed between H7 and H11 and absent between H4 and H10, indicative of S-alkylation rather than N-alkylation. Furthermore, a three bond connectivity was shown between C8 and H11 and absent between C9 and H10 in the heteronuclear multiple bond correlation (HMBC) experiment. If the product 7a was N,N'-dialkylated, a three bond connectivity would have been observed between C9 and H10. (formula presented)
16. 10. Previously, another heterocycle, benzimidazole, has been prepared from o-phenylenediamine on a solid support; see Phillips, G.B.; Wei, G.P. Tetrahedron Lett. 1996, 37, 4887-4890.