Transformations of beta-aryl-N-Cbz-alpha,beta-didehydro-alpha-amino esters with hydrazine hydrate

Drev Miha; Groselj Uros; Svete Jurij

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Transformations of beta-aryl-N-Cbz-alpha,beta-didehydro-alpha-amino esters with hydrazine hydrate

机译：β-芳基-N-Cbz-α，β-二氢-α-氨基酯与水合肼的转化

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Cyclizations of Cbz-protected alpha,beta-didehydro-beta-arylalanine esters 1 with excess hydrazine hydrate afforded mixtures of the expected 3-pyrazolidinones 2 and the unexpected 1-amino-5-benzylidenehydantoins 6 and N-Cbz-beta-arylalanine hydrazides 7. Presumably, the pyrazolidinones 2 and hydantoins 6 are formed as primary products via competitive 1,2- and 1,4-addition of hydrazine hydrate followed by cyclization, whereas beta-arylalanine hydrazides 7 are formed as secondary products via reductive cleavage of the C(5)-N(1) bond in pyrazolidinones 2. The overall selectivity depends on the reaction time and on the beta-substituent in the starting dehydroalanine ester 1.

机译：用过量的水合肼将Cbz保护的α，β-二氢-β-芳基丙氨酸酯1环化，得到预期的3-吡唑烷酮2和意外的1-氨基-5-亚苄基乙内酰脲6和N-Cbz-β-芳基丙氨酸酰肼7的混合物。推测，吡唑烷酮2和乙内酰脲6是通过水合肼的1,2-和1,4-竞争性加成然后环化而形成的初级产物，而β-芳基丙氨酸酰肼7是通过C的还原裂解形成的次级产物。吡唑烷酮2中的（5）-N（1）键。总选择性取决于反应时间和起始脱氢丙氨酸酯1中的β-取代基。

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《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2016年第6期|共9页
作者
Drev Miha; Groselj Uros; Svete Jurij;
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正文语种 eng
中图分类化学;
关键词
amino acids; cyclization; hydantoins; pyrazolidinones; reduction;

机译：氨基酸;环化;乙内酰脲;吡唑烷酮;还原;

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1. Transformations of beta-aryl-N-Cbz-alpha,beta-didehydro-alpha-amino esters with hydrazine hydrate [J] . Drev Miha, Groselj Uros, Svete Jurij Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences . 2016,第6期

机译：β-芳基-N-Cbz-α，β-二氢-α-氨基酯与水合肼的转化
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Transformations of beta-aryl-N-Cbz-alpha,beta-didehydro-alpha-amino esters with hydrazine hydrate

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