Synthesis of methylenebisamides using CC- or DCMT-activated DMSO

Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-a...
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Autor*in:	Qiang Wang [verfasserIn] Lili Sun [verfasserIn] Yu Jiang [verfasserIn] Chunbao Li [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2008

Schlagwörter:	amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine

Übergeordnetes Werk:	In: Beilstein Journal of Organic Chemistry - Beilstein-Institut, 2005, 4(2008), 1, p 51
Übergeordnetes Werk:	volume:4 ; year:2008 ; number:1, p 51

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3762/bjoc.4.51

Katalog-ID:	DOAJ071539913

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520			\|a Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive.
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allfields	10.3762/bjoc.4.51 doi (DE-627)DOAJ071539913 (DE-599)DOAJd1008373fadb40828c7368101a13fcaa DE-627 ger DE-627 rakwb eng QD241-441 Qiang Wang verfasserin aut Synthesis of methylenebisamides using CC- or DCMT-activated DMSO 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry Lili Sun verfasserin aut Yu Jiang verfasserin aut Chunbao Li verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 4(2008), 1, p 51 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:4 year:2008 number:1, p 51 https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/article/d1008373fadb40828c7368101a13fcaa kostenfrei https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2007 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2008 1, p 51
spelling	10.3762/bjoc.4.51 doi (DE-627)DOAJ071539913 (DE-599)DOAJd1008373fadb40828c7368101a13fcaa DE-627 ger DE-627 rakwb eng QD241-441 Qiang Wang verfasserin aut Synthesis of methylenebisamides using CC- or DCMT-activated DMSO 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry Lili Sun verfasserin aut Yu Jiang verfasserin aut Chunbao Li verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 4(2008), 1, p 51 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:4 year:2008 number:1, p 51 https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/article/d1008373fadb40828c7368101a13fcaa kostenfrei https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2007 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2008 1, p 51
allfields_unstemmed	10.3762/bjoc.4.51 doi (DE-627)DOAJ071539913 (DE-599)DOAJd1008373fadb40828c7368101a13fcaa DE-627 ger DE-627 rakwb eng QD241-441 Qiang Wang verfasserin aut Synthesis of methylenebisamides using CC- or DCMT-activated DMSO 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry Lili Sun verfasserin aut Yu Jiang verfasserin aut Chunbao Li verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 4(2008), 1, p 51 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:4 year:2008 number:1, p 51 https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/article/d1008373fadb40828c7368101a13fcaa kostenfrei https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2007 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2008 1, p 51
allfieldsGer	10.3762/bjoc.4.51 doi (DE-627)DOAJ071539913 (DE-599)DOAJd1008373fadb40828c7368101a13fcaa DE-627 ger DE-627 rakwb eng QD241-441 Qiang Wang verfasserin aut Synthesis of methylenebisamides using CC- or DCMT-activated DMSO 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry Lili Sun verfasserin aut Yu Jiang verfasserin aut Chunbao Li verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 4(2008), 1, p 51 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:4 year:2008 number:1, p 51 https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/article/d1008373fadb40828c7368101a13fcaa kostenfrei https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2007 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2008 1, p 51
allfieldsSound	10.3762/bjoc.4.51 doi (DE-627)DOAJ071539913 (DE-599)DOAJd1008373fadb40828c7368101a13fcaa DE-627 ger DE-627 rakwb eng QD241-441 Qiang Wang verfasserin aut Synthesis of methylenebisamides using CC- or DCMT-activated DMSO 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry Lili Sun verfasserin aut Yu Jiang verfasserin aut Chunbao Li verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 4(2008), 1, p 51 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:4 year:2008 number:1, p 51 https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/article/d1008373fadb40828c7368101a13fcaa kostenfrei https://doi.org/10.3762/bjoc.4.51 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2007 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 4 2008 1, p 51
language	English
source	In Beilstein Journal of Organic Chemistry 4(2008), 1, p 51 volume:4 year:2008 number:1, p 51
sourceStr	In Beilstein Journal of Organic Chemistry 4(2008), 1, p 51 volume:4 year:2008 number:1, p 51
format_phy_str_mv	Article
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topic_facet	amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine Science Q Organic chemistry
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container_title	Beilstein Journal of Organic Chemistry
authorswithroles_txt_mv	Qiang Wang @@aut@@ Lili Sun @@aut@@ Yu Jiang @@aut@@ Chunbao Li @@aut@@
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callnumber-first	Q - Science
author	Qiang Wang
spellingShingle	Qiang Wang misc QD241-441 misc amides misc condensation misc DMSO misc methylenebisamides misc 2,4,6-trichloro[1,3,5]triazine misc Science misc Q misc Organic chemistry Synthesis of methylenebisamides using CC- or DCMT-activated DMSO
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topic_title	QD241-441 Synthesis of methylenebisamides using CC- or DCMT-activated DMSO amides condensation DMSO methylenebisamides 2,4,6-trichloro[1,3,5]triazine
topic	misc QD241-441 misc amides misc condensation misc DMSO misc methylenebisamides misc 2,4,6-trichloro[1,3,5]triazine misc Science misc Q misc Organic chemistry
topic_unstemmed	misc QD241-441 misc amides misc condensation misc DMSO misc methylenebisamides misc 2,4,6-trichloro[1,3,5]triazine misc Science misc Q misc Organic chemistry
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title	Synthesis of methylenebisamides using CC- or DCMT-activated DMSO
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title_full	Synthesis of methylenebisamides using CC- or DCMT-activated DMSO
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title_sort	synthesis of methylenebisamides using cc- or dcmt-activated dmso
callnumber	QD241-441
title_auth	Synthesis of methylenebisamides using CC- or DCMT-activated DMSO
abstract	Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive.
abstractGer	Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive.
abstract_unstemmed	Bisamides are key fragments for the introduction of gem-diaminoalkyl residues into retroinverso pseudopeptide derivatives and in the synthesis of peptidomimetic compounds. The literature methods for these types of compounds have certain drawbacks. In particular, when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive.
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container_issue	1, p 51
title_short	Synthesis of methylenebisamides using CC- or DCMT-activated DMSO
url	https://doi.org/10.3762/bjoc.4.51 https://doaj.org/article/d1008373fadb40828c7368101a13fcaa https://doaj.org/toc/1860-5397
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Synthesis of methylenebisamides using CC- or DCMT-activated DMSO

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