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Production of novel isoquinoline-containing functional reagents and new developmet

新型含异喹啉功能试剂的生产及新进展

基本信息

批准号：
15590019
负责人：
TAKAHATA Hiroki
金额：
$ 2.24万
依托单位：
Tohoku Pharmaceutical University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2003
资助国家：
日本
起止时间：
2003 至 2005
项目状态：
已结题

项目摘要

We reported a novel and chemoselective tert-butoxycarbonylation reagent, 1-tert-butoxy-2-tert-butoxycarbonyl-1, 2-dihydroisoquinoline (BBDI), which was easily prepared in quantitative yield by the reaction of isoquinoline with Boc_2O. BBDI effected easily the tert-butoxycarbonylation for acidic substrates in the absence of bases rather than basic ones, while that for acidic compounds such as phenols, carboxylic acids using Boc_2O required some base. The synthesis of carboxylic esters is one of the most fundamental and pivotal protocols for producing natural and synthetically useful compounds in organic chemistry. The coupling reactions between activated derivatives of carboxylic acids and alcohols have been employed. These procedures are of considerable interest, especially as relate to the manipulation of peptides or complicated biologically active compounds such as macrolides. A simple and mild esterification of N-protected amino acids using BBDI as a novel condensing reagent in a on … More e-pot method was developed. This protocol has several advantages including the use of nearly equimolar amounts of alcohols, no requirement for additives, and no racemization occurs. Next, we developed a novel BBDI-catalyzed esterification of N-protected amino acids in the presence of Boc_2O under simple and mild conditions. Although a variety of methods for acid-catalyzed esterification reactions have been reported, the use of a nearly neutral catalyst such as BBDI has not been extensively investigated. Further, it was found that catalytic esterification using BBDI typed reagent derived from electron-rich isoquinoline such as 6-methoxyisoquinoline shortened a reaction time. The synthesis of carboxylic amide is one of the most fundamental and pivotal protocols for producing natural and synthetically useful compounds such as peptides in organic chemistry. We succeeded a simple and mild amidation that uses nearly equimolar amounts of a variety of carboxylic acids and amines and BBDI without the need for any additives. Less

本文报道了一种新的叔丁氧基羰基化试剂1-叔丁氧基-2-叔丁氧基羰基-1，2-二氢异喹啉（BBDI），它是由异喹啉与Boc_2O反应合成的。BBDI对酸性底物的叔丁氧羰基化反应在无碱条件下比碱性底物更容易进行，而对酚类、羧酸类等酸性化合物的叔丁氧羰基化反应则需要一定的碱。羧酸酯类化合物的合成是有机化学中生产天然和合成有用化合物的最基本和关键的方法之一。羧酸和醇的活化衍生物之间的偶联反应已经被采用。这些程序是相当感兴趣的，特别是涉及肽或复杂的生物活性化合物如大环内酯类的操作。以BBDI为新型缩合剂，在碱性条件下， ...更多信息开发了e-pot方法。该方案具有几个优点，包括使用几乎等摩尔量的醇，不需要添加剂，并且不发生外消旋化。接下来，我们发展了一种新的BBDI催化的N-保护氨基酸的酯化反应，在Boc_2O存在下，在简单和温和的条件下。虽然已经报道了用于酸催化酯化反应的各种方法，但是使用接近中性的催化剂如BBDI还没有被广泛研究。此外，发现使用衍生自富电子异喹啉如6-甲氧基异喹啉的BBDI型试剂的催化酯化缩短了反应时间。酰胺类化合物的合成是有机化学中合成多肽类化合物的基础和关键步骤之一。我们成功地进行了简单而温和的酰胺化反应，该反应使用了几乎等摩尔量的各种羧酸和胺以及BBDI，而不需要任何添加剂。少