Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation

C.R. Alonso-Cruz, A.R. Kennedy, M.S. Rodriguez, E. Suarez

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.
LanguageEnglish
Pages4116-4122
Number of pages6
JournalJournal of Organic Chemistry
Volume73
Issue number11
DOIs
Publication statusPublished - 6 Jun 2008

Fingerprint

Azirines
Azides
Thermolysis
Benzene
Iodine
alkoxyl radical

Keywords

  • nucleophilic-substitution reactions
  • resolution nmr-spectroscopy
  • diels-alder reactions
  • x-ray-structure
  • vinyl azides
  • convenient synthesis
  • stereospecific introduction
  • allylic substitutions
  • asymmetric-synthesis
  • dysidea-fragilis

Cite this

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title = "Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation",
abstract = "The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.",
keywords = "nucleophilic-substitution reactions, resolution nmr-spectroscopy, diels-alder reactions, x-ray-structure, vinyl azides, convenient synthesis, stereospecific introduction, allylic substitutions, asymmetric-synthesis, dysidea-fragilis",
author = "C.R. Alonso-Cruz and A.R. Kennedy and M.S. Rodriguez and E. Suarez",
year = "2008",
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journal = "Journal of Organic Chemistry",
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Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation. / Alonso-Cruz, C.R.; Kennedy, A.R.; Rodriguez, M.S.; Suarez, E.

In: Journal of Organic Chemistry, Vol. 73, No. 11, 06.06.2008, p. 4116-4122.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation

AU - Alonso-Cruz, C.R.

AU - Kennedy, A.R.

AU - Rodriguez, M.S.

AU - Suarez, E.

PY - 2008/6/6

Y1 - 2008/6/6

N2 - The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.

AB - The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.

KW - nucleophilic-substitution reactions

KW - resolution nmr-spectroscopy

KW - diels-alder reactions

KW - x-ray-structure

KW - vinyl azides

KW - convenient synthesis

KW - stereospecific introduction

KW - allylic substitutions

KW - asymmetric-synthesis

KW - dysidea-fragilis

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DO - 10.1021/jo800182y

M3 - Article

VL - 73

SP - 4116

EP - 4122

JO - Journal of Organic Chemistry

T2 - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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ER -