PHOTOCHEMICAL REACTIONS AND CHEMICAL EVOLUTION OF PURINES AND NICOTINAMIDE DERIVATIVES

被引:38
作者
FERRIS, JP
KUDER, JE
CATALANO, AW
机构
[1] Department of Chemistry, Rensselaer Polytechnic Institute, Troy
关键词
D O I
10.1126/science.166.3906.765
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The photochemical rearrangement of a tetramer of hydrogen cyanide to 4-aminoimidazole-5-carbonitrile, a critical step in the proposed prebiotic synthesis of purines, proceeds in high yield in the absence of oxygen without photodestruction of the reaction product. The mechanism of the rearrangement involves the conversion of the excited singlet of the hydrogen cyanide tetramer to 2-imino-3-cyano-4-aminoazetine, which then rearranges to the imidazole product. The photolysis of the vinylogous enaminonitrile 1,3-dicyano-4-amino-1, 3-butadiene yields 6-aminonicotinonitrile. The latter reaction affords an efficient route to a nicotinamide derivative from cyanoacetylene.
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页码:765 / &
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