Preparation of new nitrogen-bridged heterocycles. 59.1) syntheses and intramolecular interactions of 3-(acylmethylthio)- and 3-[(3-ethoxycarbonyl-2-propenyl)thio]thieno[3,4-b]indolizine derivatives

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 1, 2007, Pages 95-101

  Kakehi, Akikazu ^a   Suga, Hiroyuki ^a   Isogai, Hirohide ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

Anti form; Arene interaction; Gauche form; Thieno 3,4 b indolizine; UV spectra; X ray analysis

Indexed keywords

ETHYL 1 (4 BROMOBENXZOYL) 3 (2 CYANOETHYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 BROMOBENZOYL) 3 (2 CYANOETHYLTHIO) 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 BROMOBENZOYL) 3 (4 BROMOPHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 BROMOBENZOYL) 3 (4 CHLOROPHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 BROMOBENZOYL) 3 (ETHOXYCARBONYLMETHYLTHIO)THIENO[3,4 B]INDOLIZINE CARBOXYLIC ACID; ETHYL 1 (4 BROMOBENZOYL) 3 [(3 ETHOXYCARBONYL 2 PROPENYL)THIO]THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 (2 CYANOETHYLTHIO) 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 (4 CHLOROPHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 (ETHOXYCARBONYLMETHYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 (ETHOXYCARBONYLMETHYLTHIO)THIENO[3,4 B]INDOLIZINE CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 (PHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) 3 [(3 ETHOXYCARBONYL 2 PROPENYL)THIO]THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHLOROBENZOYL) E (2 CYANOETHYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 (4 CHROMOBENZOYL) 3 (PHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (2 CYANOETHYLTHIO) 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (2 CYANOETHYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (4 BROMOPHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (4 CHLOROPHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (ETHOXYCARBONYLMETHYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 (PHENACYLTHIO)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 1 BENZOYL 3 [(3 ETHOXYCARBONYL 2 PROPENYL)THIO]THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 (4 BROMOPHENACYLTHIO) 1 (4 CHLOROBENZOYL)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 (4 BROMOBENZOYL) 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 (4 BROMOBENZOYL)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 (4 CHLOROBENZOYL) 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 (4 CHLOROBENZOYL)THIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 BENZOYL 7 METHYLTHIENO[3,4 B]INDOLIZINE 9 CARBOXYLIC ACID; ETHYL 3 ACETONYLTHIO 1 BENZOYLTHIENO[3,4 B]INDOZILINE 9 CARBOXYLIC ACID; INDOLIZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DEHYDROGENATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

HETEROCYCLIC COMPOUNDS; INDOLIZINES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITROGEN; SPECTROPHOTOMETRY, INFRARED;

EID: 33846081976     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.95     Document Type: Article

References (12)

1. For part 58 of this series, see Kakehi A., Suga H., Kaneko Y., Fujii T., Tanaka N., Chem. Pharm. Bull., 53, 1430-1438 (2005).
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8. The formation energies (FEg and FEa) for the opitimized gauche and anti conformations are as follows: ethyl methyl sulfide (FEg= -15.1451 kcal/mol and FEa=-14.1033 kcal/mol); benzyl methyl sulfide (FEg=17.9939 kcal/mol and FEa=19.4272 kcal/mol); ethyl phenyl sulfide (FEg=18.8116 kcal/mol and FEa=20.2082).
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