REGIOSELECTIVE SYNTHESIS OF 3-INDOLYL(ALKOXY)ACETATES

The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products...

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Published inHeterocycles Vol. 81; no. 5; pp. 1169 - 1182
Main Authors Suarez-Castillo, Oscar R., Melendez-Rodriguez, Myriam, Cano-Escudero, Indira C., Luz De Ita-Gutierrez, Sandra, Sanchez-Zavala, Maricruz, Morales-Rios, Martha S., Joseph-Nathan, Pedro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
ALKYLATION
STEREOCONTROLLED TOTAL-SYNTHESIS
BISINDOLE ALKALOIDS
CARBONYL-COMPOUNDS
GLYOXYLATE
FRIEDEL-CRAFTS REACTION
ENANTIOSPECIFIC TOTAL-SYNTHESIS
DERIVATIVES
INDOLES
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Abstract The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of alpha-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give alpha-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.
AbstractList The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of alpha-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give alpha-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.
Author Morales-Rios, Martha S.
Melendez-Rodriguez, Myriam
Sanchez-Zavala, Maricruz
Suarez-Castillo, Oscar R.
Cano-Escudero, Indira C.
Luz De Ita-Gutierrez, Sandra
Joseph-Nathan, Pedro
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  givenname: Martha S.
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  givenname: Pedro
  surname: Joseph-Nathan
  fullname: Joseph-Nathan, Pedro
  organization: Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
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CitedBy_id crossref_primary_10_1021_acs_joc_5b01736
crossref_primary_10_3987_COM_23_14891
crossref_primary_10_1016_j_tetasy_2012_08_005
crossref_primary_10_1002_chin_201040105
crossref_primary_10_1021_jo4028177
Cites_doi 10.1021/ol0262643
10.1002/adsc.200600495
10.1021/jo030116o
10.1055/s-2004-831217
10.1016/j.micromeso.2007.03.032
10.1021/np060406a
10.1021/ol020209c
10.1016/j.tet.2005.01.058
10.1021/ol061552a
10.1039/b202352k
10.1021/ol000331g
10.1002/ejoc.200700886
10.1016/j.tet.2005.07.023
10.3987/COM-08-S(F)66
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Issue 5
Keywords OXIDATION
ALKYLATION
STEREOCONTROLLED TOTAL-SYNTHESIS
BISINDOLE ALKALOIDS
CARBONYL-COMPOUNDS
GLYOXYLATE
FRIEDEL-CRAFTS REACTION
ENANTIOSPECIFIC TOTAL-SYNTHESIS
DERIVATIVES
INDOLES
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HEHRE WJ (WOS:000278476600006.12) 1986
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Snippet The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave...
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Chemistry, Organic
Physical Sciences
Science & Technology
Title REGIOSELECTIVE SYNTHESIS OF 3-INDOLYL(ALKOXY)ACETATES
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