Three New Synthetic Methods for the 1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indoles Having an AlkoxyGroup at the 3a-Position

Shiho Funaki, Fumio Yamada, Takako Iwaki, andMasanori Somei*

■■ COMMUNICATIONS

3a-Chloro-, 3a-Bromo-, 3a-Hydroxy-, and 3a-Alkoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles

1811

NR1

NHCO2Me

N

X

HOMe

NCO2Me

N

R3

HR2

NCO2Me

R1 = OH, OMeR2 = Ac, OMeR3 = OH, OMe, OEt, O-allyl O-benzyl, O-2-hydroxyethyl, OAc

Synthetic Models Related to Furanocoumarin — CYP3A4 Interactions. Synthesis of Furanocoumarin Dimers that Have Inhibitory Effects on Activity of Human CYP3A4

Naozumi Nishizono, Minoru Machida, Keiji Wada,Teruki Yoshimura, Yuki Yamaguchi, Hitomi Kasai,and Kazuaki Oda*

Paradisin Grapefruit Juice Residual Activity P450

1817

O O

OOO O

OO

CYP3A4 IC50=0.02 µM

High Throughput Synthesis of Pyrazolopyrimidinesvia Copper-catalysed Cyclization and X-Ray Study

Muhammad Usman Anwar, Klaus Eichele,Mustafa M. El-Abadelah, Samer Al-Gharabli,Monther Khanfar, Raid J. Abdel-Jalil, andWolfgang Voelter*

■■ PAPERS

Pyrazolopyrimidine Phosphodiesterase Inhibitor Viagra® Erectyle Dysfunction Copper-catalysed Cyclization

1821

H2NOC

H2N

NN

Me

HN

N

O

Ar

NN

Me

A Convenient Preparaion of a Series of 2-Aryl-substitutedImidazolidines through Diamine Transfer Reaction

Chizhong Xia, Yongbin Zhang, Donghong Li, and Wei Guo*

Aryl Transfer Reaction 2-Aryl-substituted Imidazolidine Aromatic Aldehyde n-Butylamine

1829

NN Me

Me

R ArCHOn-BuNH2 NN MeR

MeCN, reflluxing

Ar

HETEROCYCLES, Vol. 65, No. 8, 2005

A New !-Glucosidase Inhibiting DithiadiazetidinDerivative from Symplocos racemosaKlaus-Peter Zeller, M. Iqbal Choudhary, Umar Farooq, Shamsun Nahar Khan, Muhammad Abid Rashid,Muhammad Zubair, Muhammad Athar Abbasi, andViqar Uddin Ahmad*

Dithiadiazetidin NMR-Technique Symplocaceae Symplocos racemosa !-Glucosidase

1837

N CH2

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2

CH2

CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

1

3 1' 3'

11'1

31'3'

11'

N

S S

CH2CH2CH2 CH2 C

O

O CH2CH2 CH2 C CH2

OO

1

Selective Reduction of Nitrocinnamoylfumagillols with!,"-Unsaturated Ester Using Borohydride ExchangeResin (BER)-Nickel Acetate

Sang Joon Lee, Soon Kil Ahn, Sung Kwon Kang,Jung Hwa Lee, Joong Bok Ahn, and Hong Woo Lee*

Chemoselective Reduction Nitrocinnamoylfumagillol Derivative Borohydride Exchange Resin(BER)-Ni(OAc)2

1843

R2

NO2

O

O

O

O

HOMe

R1

R2

NH2

R1 =

R2 = Cl, OMe

Yields : 85-95%

Reaction of Polychloroacetamides with Amines: Reductive Dechlorination and Aziridine Formation

Okiko Miyata, Masafumi Ueda, Ayako Saito, andTakeaki Naito*

Aziridine Reductive Dechlorination Single-Electron Transfer DBU Trichloroacetamide

1857

NOBnCl

BnN

Cl

O

Clamine

N

HCl NOBnCl

OBn

N

Cl

OBn

NOBn

+

Synthesis and Antimicrobial Activity of Some New Pyridazine Derivatives

Ionel I. Mangalagiu, Roxana M. Butnariu, Maria D. Caprosu, and Ionel I. Mangalagiu*

Pyridazine Antimicrobial Ylide Cycloaddition Microwave

1871

NN

CHCOC6H4Cl-4

NN

CH COC6H4Cl-4

New Syntheses of 1-Benzoyltetrahydroisoquinoline Derivatives Using Polymer-supported Bis(trifluoro-acetoxyiodo)benzene

Huey-Min Wang, Rei-Sheu Hou, Hsin-Yu Huang, andLing-Ching Chen*

Pictet-Spengler Reaction Pummerer-Type Reaction Iminium Cation

1881

R2

R3

R4HN

Ts

PSBTI

ClCH2CH2Cl

R2

R3

R4

R1 O

NTs

PhSCH2COR1

HETEROCYCLES, Vol. 65, No. 8, 2005

Regio- and Stereoselective Cycloadditions and Further Transformations of Azomethine Imine Derivatives of Fused [1,2,4]Triazines

Antal Csámpai, Csilla Gróf, Branko Stanovnik,Orsolya Egyed, Zsuzsanna Riedl, and György Hajós*

1,3-Dipolar Cycloaddition Regioselectivity Stereoselectivity Mesomeric Betaine Ring Opening

1889

N

NHN

OMe

Me

NN

BF4

CN

NC

N

NNMe

NHN

CN

H

CN

OMe

CH2Cl2, Et3Nrt, 10 h

Synthesis of 2-Selenoxo-1,3-thiazolidin-4-onesand 2-Selenoxo-1,3-thiazinan-4-ones from Isoselenocyanates

Anthony Linden, Geoffroy L. Sommen, andHeinz Heimgartner*

Cyclization Isoselenocyanate Selenorhodanine Selone

1903

Ar N C Se

HS XCO2H

SX

NO SeAr

EtOH, H2O

rt

Allylation of Meldrum’s Acids by Allylic Alcohols Using Tetrakis[triphenylphosphine]palladium(0) Catalysts

Hsin-Yu Huang, Huey-Min Wang, Rei-Sheu Hou, andLing-Ching Chen*

Palladium-catalyzed Reaction Allylic Alcohol 5-Allylated Meldrum’s Acid

1917

OHO O

OR2 H

O

O O

OR2

OR1

R1

1 2 3

(PPh3)4Pd

benzene , reflux

Total Synthesis of Styelsamine C, and Formal Synthesis of Norsegoline

Akinori Kubo and Shinsuke Nakahara*

Styelsamine C Norsegoline Synthesis Intramoleculer Nitrene Insertion Biaryl Cross Coupling

1925

NO2Me

OMeNH2 N

NO2Me

OMeN

HNR1OC

OR2

norsegoline R1 = OMe ; R2 = Mestyelsamine R1 = R2 = H

HETEROCYCLES, Vol. 65, No. 8, 2005

The Library of Cinchona Alkaloids-1,2,3-triazole Derivatives: Structure and Facile Access by “Click Chemistry”

Jacek Gawronski, Urszula Rychlewska, Agnieszka Plutecka, Michal Migas, and Karol Kacprzak*

■■ NOTES

Cinchona Alkaloid 1,2,3-Triazole Click Chemistry 1,3-Dipolar Cycloaddition Huisgen Cycloaddition

1931

N

NOMe

H

N

(H)R1R2

9-azido Cinchona alkaloids + alkynes

"clickchemistry"

16 new 1,2,3-triazoles

NN

5H-[1,2,5]Selenadiazolo[3,4-f]indole as a MaskedForm of 5,6-Diaminoindole

Jealux Okwakol and Spiros Grivas*

2,1,3-Benzoselenadiazole Indoline Deselenation Batcho-Leimgruber Pyrroloquinoxaline

1939

O2N NH N

AcNH

N2H4

H2N

H2N

NH

4 steps 2 stepsRaney Ni

NSe

N

NSe

N

Syntheses and Crystal Structures of Diethylated DaidzeinSulfonates

Qiu-Ya Wang and Zun-Ting Zhang*

Daidzein Crystal Structure Hydrogen Bond Aromatic "-" Stacking

1947

Et2SO4

H2SO4NaCl

A C

BOHO

OOH

OEtO

OOEt

SO3Na

OEtO

OOEt

Microwave-assisted and Efficient One-Pot Synthesis of Substituted 1,2,4-Triazoles

Hongli Bao, Daliang Li, and Tianpa You*

Triazole One-Pot Reaction Microwave-assisted Reaction Solvent-free

1957

RNH2MWAcNHNH2 Me2NCH(OMe)2

N

N

N

MeR2

New Coumarins from the Ailanthus altissimaMin Suk Yang, Hyun Sook Kwon, Jun Lee, Jong Rok Lee, Seon Woo Hwang, and Ki Hun Park*

Ailanthus altissima Altissimacoumarin A Altissimacoumarin B Isofraxidin Coumarin

1963

O OOOMe

OMeO

HO

O OOOMe

MeOO

1

2

HETEROCYCLES, Vol. 65, No. 8, 2005

A Practical Synthesis of 8-Hydroxyacyclovir and9-(Carboxymethoxymethyl)guanine, Metabolitesof Acyclovir

Shiroshi Shibuya, Takehiro Yamagishi, Noriaki Shiina,Hiroyuki Ouchi, Yasuo Sakai, Teruo Kutsuma, andTsutomu Yokomatsu*

Acyclovir Metabolite Large Scale Synthesis Tautomer 13C NMR Spectrum

1967

HN

N

N

N

O

H2N O OH

OHHN

N

N

N

O

H2N O CO2H

8-hydroxyacyclovir CMMG

Synthesis of 2,4-Diarylimidazoles through SuzukiCross-coupling Reactions of Imidazole Halides with Arylboronic Acids

Ingo Langhammer and Thomas Erker*

Lithiation Selective First Arylation Selective Second Arylation MOM Protecting Group SEM Protecting Group

1975

N

N

PGNH

N

Aryl1 Aryl2Hal

An Efficient Synthesis of Bergapten

Minoru Machida, Keiji Wada, Teruki Yoshimura,Yuki Yamaguchi, Yukio Tamai, Naozumi Nishizono,and Kazuaki Oda*

Furanocoumarin Regioselective Iodination Oxdative Cleavage Cyclization

1985

OH

HO OH O O

OMe

O

Tautomerization of 3a,7a-Dihydroindole-2,3,3a,4-tetracarboxylate

Ji Sook Yu, Kyu Ok Jeon, and Chang Kiu Lee*

Tautomerism 3a,7a-Dihydroindole Indoline

1989

NH

EE E

EN

E E E

EN

E E E

E

E = CO2Me

+

Synthetic Study toward Pancracine

Chun-Li Pai, Chun-Yu Lin, Hua-Ping Chen, andMeng-Yang Chang*

Pancracine trans-(2S,4R)-4-Hydroxyproline Formal Synthesis One-Pot Synthesis Intramolecular Aldol Condensation

1999

N

O

O

OH

OH

H NTs

O

O

NH

HO

CO2HS

pancracine

known

HETEROCYCLES, Vol. 65, No. 8, 2005

Recent Progress of Halogen-Dance Reactions in Heterocycles

Zhan-Bin Zhang, Xin-Fang Duan, and Xinfang Duan*

■■ REVIEW

Halogen-Dance Halogen Migration Aromatic Halide

2005

X

X

EHetero-Aryl

base

EHetero-Aryl

201320172027204320452051

PolyketidesAromaticsTerpenesSteroidsAlkaloidsMiscellaneous

■■ NEW HETEROCYCLIC NATURAL PRODUCTS

2055 Erratum

■■ ANNAOUNCEMENT

HETEROCYCLES, Vol. 65, No. 8, 2005