The paper extends a previously published report [4] on chemical properties of a -amino nitriles and of members of the C3H,N2 ensemble (Scheme I ) as observed in experiments carried out under non-aqueous conditions. The reactions investigated and the observations made are summarized in some detail in the English footnotes (*) referring to Schemes 1-17 and Fig. 1. Schenw 3 *) QCN H 18 CN QCN NC 19 H NC iN NHz HN flyN HzN 15 21 1 *) Retrosynthetic analysis of the structural relationship between the nitrile form of 1,4-dihydronicotinamide, and the glutamic and aspartic acid dinitriles. The relationship rests on the equivalence of glutamic acid dinitrile and acrolein imine under thermal conditions. *) Uber eine potentiell prabiotische Bildung von Asparaginsaure aus Cyanoacetylen mit HCN, NH3 in H,O vgl. Sanchez et ul. [lo]. 9, Eine Variante der Herstellung von 20 aus 22 und 4-Oxobutannitril ist in [4] beschrieben.Scheme 5 *) 2217 *) Hypothetical reaction paths to products in the FVP of (E/Z)-19 and 20. Within this framework of structural transformations, the nitrile form of 1,4-dihydronicotinamide is at the same oxidation level as the ensemble of the dinitrile forms of glutamic and aspartic acids. e-") Gestutzt wird diese Interpretation der Reaktionsmechanismen durch die Beobachtung, dass auch die hier nicht explizit beschriebene Pyrolyse des strukturvenvandten N-Propenylidenasparagindinitril (3-Azahexa-3,5-dien-1,2-dicarbonitril) zu den gleichen isolierbaren Produkten, ausschliesslich 26 und 27, fuhrt, wahrend die Pyrolyse von N-(I-Cyanoethy1iden)glutamindinitril (cl-Azahex-4-en-l,3,5-tricarbonitril) nur 26 und 29und 5-Methylpyrrol-2-carbonitril liefert (121, S . 62,68, 188, 199).

2-Aminopropenenitrile in solvents such as MeCN, MeOH, or H2O is photoisomerized by UV light to racemic aziridine-2-carbonitrile (rac-2); the larger part of the starting material, however, fragments to HCN and MeCN. The observed photocyclization constitutes a structural connection within an ensemble of C3H4N2 compounds considered to be potentially relevant to prebiotic chemistry.

Chemistry of α-Amino Nitriles. Part 12. Exploratory Experiments on Thermal Reactions of α-Amino Nitriles. -Flash vacuum pyrolysis of a number of α-amino nitriles is studied. Depending on the educt structure pyridine, pyrrole, indole and/or pyrazine derivatives as well as decomposition products are formed. -(XIANG, Y.-B.; DRENKARD, S.; BAUMANN, K.; HICKEY, D.; ESCHENMOSER, A.; Helv.

259ChemInform Abstract Photoisomerization of 2-aminopropenenitrile (I) leads to the aziridine (II); the larger part of the starting material, however, fragments to HCN and MeCN. The photocyclization constitutes a structural connection within an ensemble of C3H4N2 compounds considered to be potentially relevant to prebiotic chemistry.

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