62539-83-7Relevant articles and documents
A synthesis of heteroaromatic analogues of 1-methyl-1,2,3,4-tetrahydroisoquinoline using the Pummerer-type cyclization reaction: observation of tandem cyclization reaction.
Horiguchi, Yoshie,Ogawa, Keita,Saitoh, Toshiaki,Sano, Takehiro
, p. 214 - 220 (2007/10/03)
The sulfoxides 7b and 7d carrying thiophene or benzothiophene as heteroaromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction), underwent an intramolecular alkylation in an exclusive manner to yield 4,5,6,7-tetrahydro-7-methyl-4-phenylsulfanylthieno[2,3-c]pyridine-6-carbaldehyde (10) and the corresponding benzothiophene derivative (12b) in high yields, respectively. Thus, this route provides biologically interesting nitrogen heterocycles (1b) and (2b). On the other hand, the sulfoxide (7c) carrying benzofuran as a nucleophile on reaction with TFAA yielded not only the Pummerer-type cyclization product (12a), but also the diastereoisomeric tandem cyclization products (13) and (14) having a noble 11-aza-2-oxa-7-thiatricyclo[4.3.3.0(1,5)]dodecane ring system (B). The formation of these products can be readily rationalized by the intervention of the oxonium ion intermediate (21).
Pyrimidine derivatives and processes for the preparation thereof
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, (2008/06/13)
The present invention relates to novel pyrimidine derivatives of the formulae (I-1) and (I-2) and pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing same as an active ingredient, their novel intermediates, and processes for the preparation thereof: STR1 wherein: R4 and R5, which may be the same or different, are independently hydrogen or a C1 -C3 alkyl group, or jointly form a cyclopentyl or cyclohexyl ring; A is a group of formula(II): STR2 wherein R1 and R2 are, independently of each other, hydrogen or a C1 -C3 alkyl group, and R3 is hydrogen, a C1 -C3 alkyl group or a halogen; and B is 1-(substituted)-1,2,3,4-tetrahydroisoquinolin-2-yl of formula (III-1) or 7-(substituted)-4,5,6,7-tetrahydrothieno?2,3-c!pyridin-6-yl of formula (III-2) STR3 wherein R6 is hydrogen or a C1 -C3 alkyl group.