Methyl quinoline sulfide

Nitrogen-containing volatiles such as methyl anthranilate (30), methyl N-methyl anthranilate (31), indole (32), 3-methyl indole (= skatole) (33), 2-methoxy-3-iso-butylpyrazine (34), alkyl pyrazines (35), quinoline (36), methyl quinoline (37), pyridines (38), and so on sulfur-containing volatiles such as sulfides and thiophenes (e.g., dimethyl sulfide (39), dimethyl disulfide (40), diallyl disulfide (42), 3,2-dimethylthiophene (43), 4-mercapto-4-methyl pentanone (44), 8-mercapto-/ -men-than-3-one (45), l-/ -menthene-8-thiol (46), 3-mercaptohexanol (47), 5-prenylth-ioesters, thiazols, sulfides of mono- and sesquiterpenes, mint sulfide (48), isomint sulfide (49), etc.) (1, 2, 13, 14). 

Likewise, pyridines such as methyl isonicotinate 1999 or quinolines are readily oxidized by BTSP 1949 in the presence of HOReOs in CH2CI2 to give, after 6 h at 24°C, 98% yield of, e.g., methyl isonicotinate N-oxide 2000 [174] (Scheme 12.49). The oxidation of diphenylsulfide with BTSP 1949 and triphenylphosphine dichloride in acetonitrile results, after 60 h at room temperature, in only 12% diphenyl sulfoxide 2001 and 88% recovered diphenyl sulfide [175] (Scheme 12.49), whereas thianthrene 5-oxide 2002 is oxidized by the peroxy-Mo complex 2003 to give 58% of a mixture of 2004 to 2007 in which the trans 5,10-thioxide 2005 predominates [176] (Scheme 12.50). 

Thienyl sulfides with the 2-position of the thiophene ring blocked, e.g., allyl 2-methyl-3-thienyl sulfide (51), also undergo sigmatropic rearrangement when heated in quinoline [Eq. (23)]. 2,6-Dimethyl-2,3-dihydro-thieno[3,4-Z ]thiophene (52) is formed, together with other products. 

Three heterocyclic aromatic amines, 2-amino-3-methyl-imidazo[4, 5-f]quinoline (IQ),2-amino-3,4-dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, have been found in boiled pork juice [109]. Six organosulfur compoimds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulftde (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of... 

Makisumi and coworkers [15] investigated the thermal behavior of allyl 4-quino-lyl sulfides (Scheme 9.4). After heating at 200°C, 2-methyl-2,3-dihydrothieno [3,2-c]quinoline was obtained in 73% yield (Scheme 9.4). This efficient heterocycle synthesis was extended to precursors bearing a substituted allyl or propargyl chain [16]. If an amine was used as solvent, a mixture of five- and six-membered ring products was obtained [17,18]. 

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