2009
DOI: 10.1021/ja808692j
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New Synthetic Technologies for the Construction of Heterocycles and Tryptamines

Abstract: New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines (I) are sequentially converted to heterocycles II ((3-(2-aminophenyl)pyrrolidin-3-ol) derivatives), III (substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrolidines), and VI (2-(4,5-dihydro-1H-pyrrol-3-yl)aniline) derivatives through a route involving t-BuLi induced ortho-metalation/LaCl(3).2LiCl metal exchange, reaction with N-Boc pyrrolidin-3-one (5), and subsequent decarboxylativ… Show more

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Cited by 51 publications
(14 citation statements)
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“…Pyrrole-containing molecules include commonly naturally produced compounds such as chlorophyll, chlorins, vitamin B12 and porphyrinogens [34][35][36]. A pyrrole ring is also a part of tryptamines including serotonin, melatonin and many other biologically important substances [37][38][39][40]. For that reason, apart from broadening our knowledge of the stacking interaction phenomenon itself, this extensive study of the intermolecular interaction in model pyrrole systems may be relevant in electronic properties of pyrrole-unit-based drugs.…”
Section: Introductionmentioning
confidence: 99%
“…Pyrrole-containing molecules include commonly naturally produced compounds such as chlorophyll, chlorins, vitamin B12 and porphyrinogens [34][35][36]. A pyrrole ring is also a part of tryptamines including serotonin, melatonin and many other biologically important substances [37][38][39][40]. For that reason, apart from broadening our knowledge of the stacking interaction phenomenon itself, this extensive study of the intermolecular interaction in model pyrrole systems may be relevant in electronic properties of pyrrole-unit-based drugs.…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, modern approaches utilize the annulation method for the construction of the pyrrole ring. This involves the Fischer indolization of arylhydrazines with 4‐aminobutyraldehyde equivalent,11 Larock heteroannulation of o ‐haloanilines with internal alkyne,12 allyl amine,13 or substituted aldehyde14 and reaction of N‐protected anilines with pyrrolidin‐3‐one 15. Although these methods provide a viable route for the synthesis of substituted tryptamines, necessary isolation and preparation of reactants/reactive intermediates, multistep reaction sequences, and the need of a strong reducing reagent limits their potential application.…”
Section: Introductionmentioning
confidence: 99%
“…This involves the Fischer indolization of arylhydra- zines with 4-aminobutyraldehyde equivalent, [11] Larock heteroannulation of o-haloanilinesw ith internal alkyne, [12] allyl amine, [13] or substituted aldehyde [14] and reactiono fN -protected anilines with pyrrolidin-3-one. [15] Although these methods provide av iable route for the synthesis of substituted tryptamines,n ecessary isolation and preparation of reactants/reactive intermediates, multistep reactions equences, and the need of as trong reducing reagent limits their potential application. Thus, the developmento fanew efficient and operationally simple strategy for the construction of biologically important tryptamines from readily available starting materials is highly desirable.…”
Section: Introductionmentioning
confidence: 99%
“…Given the value of such heterocyclic alkenes to prepare alternative heterocyclic derivatives by reaction of the alkene, we examined their formation . Related dehydration reactions are commonly achieved in presence of acid, though there are few examples of Lewis acid catalyzed dehydration on these types of substrates , . The reaction of each heterocycle derivative 2 , 3 , 5 and 6 was investigated in the absence of the nucleophile, using FeCl 3 as catalyst (Scheme ).…”
Section: Resultsmentioning
confidence: 99%