Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization

A mild, efficient and versatile method has been developed for the construction of a functionalized natural product, meridianin, and its post conversion to pyrimido-β-carboline by cationic π- cyclization. The strategy involves the introduction of an amino group at the C-5 of the pyrimidine ring and u...

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Main Authors:	Piyush K. Agarwal, Meena D. Dathi, Mohammad Saifuddin, Bijoy Kundu
Format:	Article
Language:	English
Published:	Beilstein-Institut 2012-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cyclization indole meridianin natural products nitrogen heterocycles
Online Access:	https://doi.org/10.3762/bjoc.8.220

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spelling	doaj-e1887a3ff9d74d9588e714f94eec5d0d2021-02-02T03:26:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-11-01811901190810.3762/bjoc.8.2201860-5397-8-220Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclizationPiyush K. Agarwal0Meena D. Dathi1Mohammad Saifuddin2Bijoy Kundu3Division of Medicinal and Process Chemistry, Central Drug Research Institute, CSIR, Lucknow, 226001, India, Phone: +91 522 2612411-18; Fax: +91 522 2623405Division of Medicinal and Process Chemistry, Central Drug Research Institute, CSIR, Lucknow, 226001, India, Phone: +91 522 2612411-18; Fax: +91 522 2623405Division of Medicinal and Process Chemistry, Central Drug Research Institute, CSIR, Lucknow, 226001, India, Phone: +91 522 2612411-18; Fax: +91 522 2623405Division of Medicinal and Process Chemistry, Central Drug Research Institute, CSIR, Lucknow, 226001, India, Phone: +91 522 2612411-18; Fax: +91 522 2623405A mild, efficient and versatile method has been developed for the construction of a functionalized natural product, meridianin, and its post conversion to pyrimido-β-carboline by cationic π- cyclization. The strategy involves the introduction of an amino group at the C-5 of the pyrimidine ring and utilizing the nucleophilictiy of the C-2 in the indole ring to facilitate cationic π-cyclization.https://doi.org/10.3762/bjoc.8.220cyclizationindolemeridianinnatural productsnitrogen heterocycles
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Piyush K. Agarwal Meena D. Dathi Mohammad Saifuddin Bijoy Kundu
spellingShingle	Piyush K. Agarwal Meena D. Dathi Mohammad Saifuddin Bijoy Kundu Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization Beilstein Journal of Organic Chemistry cyclization indole meridianin natural products nitrogen heterocycles
author_facet	Piyush K. Agarwal Meena D. Dathi Mohammad Saifuddin Bijoy Kundu
author_sort	Piyush K. Agarwal
title	Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
title_short	Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
title_full	Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
title_fullStr	Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
title_full_unstemmed	Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
title_sort	engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2012-11-01
description	A mild, efficient and versatile method has been developed for the construction of a functionalized natural product, meridianin, and its post conversion to pyrimido-β-carboline by cationic π- cyclization. The strategy involves the introduction of an amino group at the C-5 of the pyrimidine ring and utilizing the nucleophilictiy of the C-2 in the indole ring to facilitate cationic π-cyclization.
topic	cyclization indole meridianin natural products nitrogen heterocycles
url	https://doi.org/10.3762/bjoc.8.220
work_keys_str_mv	AT piyushkagarwal engineeringofindolebasedtetheredbiheterocyclicalkaloidmeridianinintobcarbolinederivedtetracyclicpolyheterocyclesviaaminofunctionalization6endocationicpcyclization AT meenaddathi engineeringofindolebasedtetheredbiheterocyclicalkaloidmeridianinintobcarbolinederivedtetracyclicpolyheterocyclesviaaminofunctionalization6endocationicpcyclization AT mohammadsaifuddin engineeringofindolebasedtetheredbiheterocyclicalkaloidmeridianinintobcarbolinederivedtetracyclicpolyheterocyclesviaaminofunctionalization6endocationicpcyclization AT bijoykundu engineeringofindolebasedtetheredbiheterocyclicalkaloidmeridianinintobcarbolinederivedtetracyclicpolyheterocyclesviaaminofunctionalization6endocationicpcyclization
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Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization

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