SYNTHESIS

Journal of Synthetic Organic Chemistry

2006 No. 1 January I

Review

a,b-Dehydroamino Acids
HO
*B B* R1 R
2

C. Bonauer, T. Walenzyk, B. Knig*

O N2H

21

Short Paper

24

Papers

New Enantiomerically Pure Allylboronic Esters in Allyl Additions: Synthesis and NMR Investigation of Intermediates
J. Pietruszka,* N. Schne

R3CHO R3

O R2

Ph Ph O B* = B O OMe Ph Ph OMe

R1 dr determination via characteristic chemical shiftsm hydrolysis OH R2 R2 R1 yield: 6597% ee: 92>99%

31
O eS R 2 N 1R O + N N eS R 2 N
1

37 Generation of Cyclic Ketene-N,X-Acetals (X = O, S) from 2-Alkyl-1,3-oxazolines and 2-Alkyl-1,3-thiazolines. Reactions with Acid Chlorides, 1,3-Diacid Chlorides and N-(Chlorocarbonyl) Isocyanate
A. Zhou,* C. U. Pittman Jr.*

M. Koketsu,* M. Kogami, H. Ando, H. Ishihara*

3R

evitatitnauq ot %46 :dleiy

Preparation of 5-Acyl-2-amino-1,3-selenazoles by the Reaction of Selenazadienes with a-Haloketone

C3H

xulfer H/HOeM/DBI ro

C3H

O. Prakash,* A. Kumar, A. K. Sadana,* S. P. Singh

rA O

O
2lC2HC/BITH

rA

O HO

A Novel Synthesis of New 3-Aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones Using Hypervalent Iodine(III) Reagents

Table of Contents

VII

49 Reduction of 2,5-Bis(3-indolyl)pyrazines to 2,5-Bis(3-indolyl)piperazines: Synthesis of Bisindolylpiperazine Marine Alkaloids Dragmacidin A, B, and C

F. Tonsiengsom, F. Y. Miyake, K. Yakushijin, D. A. Horne*

55
3RO

59 Studies with Functionally Substituted Enamines: The Reactivity of Enaminals and Enamino Esters toward Naphthoquinone, Hydrazonoyl Halides, Aminoazoles and Hippuric Acid
B. AL-Saleh, S. Makhseed,* H. M. E. Hassaneen, M. H. Elnagdi

63
O O O cAO

V. Singh, S. Batra*

73
O H ,SPDBT = R H ,2HN = Y rPcHN ,2HN ,lC = X N X N

M. D. Garca, O. Caamao,* F. Fernndez, P. Abeijon, J. M. Blanco

OSPDBT N N eM N N OH

81 Synthesis of Novel Diethyl Indolylphosphonates and Tetraethyl Indolyl-1,1-bisphosphonates by Michael Addition

H. Couthon-Gourvs,* G. Simon, J.-P. Haelters, B. Corbel

N O NH

H ,SPDBT = R

eM

OR

2HN

31

eM

OR

Synthesis of New 1(N)-Homocarbanucleosides Based on 1-Methylcyclopenta[c]pyrazole Scaffold

top eno

O2H eM2OC

eM2OC

OH

Convenient Synthesis of Substituted a-Methylene-d-valerolactones in Aqueous Medium Using BaylisHillman Chemistry

dleiy %4938

G. V. M. Sharma,* K. L. Reddy, P. S. Lakshmi, P. R. Krishna

2R

1R

H N

O3R

cAO4HN

TCT

3RO

OHC-1R

In situ Generated HCl An Efficient Catalyst for Solvent-Free Hantzsch Reaction at Room Temperature: Synthesis of New Dihydropyridine Glycoconjugates

Papers

VIII

Table of Contents

89

Papers

C. Schmuck,* D. Rupprecht, C. Urban, N. Walden

97
n)2RN(

V. I. Sorokin,* V. A. Ozeryanskii, G. S. Borodkin

103
N
3FC

107
)3rPi(iS N R lC
2lC2HC

111
1

115 Azetidin-2,3-dione Synthon for Stereoselective Synthesis of cis- and trans-C-3-Alkyl/Aryl Azetidin-2-ones
D. K. Tiwari, V. K. Gumaste, A. R. A. S. Deshmukh*

fTO ,I ,rB ,lC = X ;uB-t ,hP = 2R ;tE ,eM = 1R ;W ,oM = 1M ;nI ,aG ,lA = M

M. Shenglof, G. A. Molander, J. Blum*

3 RP 2

,2])3hPP(3)OC( )pc(1MdP[ )1 X

lCH qa )2

2 eM

eM

1R

1R

Cross-Coupling of Aryl Halides and Triflates with Group 13-Metal Alkylating Reagents by Palladium Molybdenum and PalladiumTungsten Mixed-Metal Catalysts

hP2OS = R

V. Nair,* R. Dhanya, N. Vidya, S. Devipriya

,2lCnZ

)3rPi(iS

RN +

RN

2lC2HC lC ,2lCnZ RHN

RHN

hPOC = R

lC

Lewis Acid Catalyzed Addition of Allylsilane to o-Quinonediimides: Formal DielsAlder Reaction versus Allylation

rA

4H6CrBp

rA

= rA

rA

C. Brul, J.-P. Bouillon, E. Nicola, C. Portella*

HN

3FC

3FC

Synthesis of Original Trifluoromethylated 6-Aryl-pyridazines Fused with Thiazolidine or 1,2,4-Triazole

n)N2R(

rA +aN

n)2RN(

n)N2R(

A New Route to Polykis(dialkylamino)benzenes and -naphthalenes Based on Protodefluorination of Electron-Rich Fluoroaromatics: Anion Radicals of Arenes as a Simple and Effective Alternative to Classical LAH-Based Systems

.tac/2H O O O H N O

HO O
+H

Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds

Table of Contents

IX

123

128
HO
2R

R. Nadano, J. Ichikawa*

133
2R 3R

146
rB
3FC2OS

B. J. Coe,* N. R. M. Curati, E. C. Fitzgerald

151
2RS

156
N N
1R

2R

%6937

OHC ,lC2HC ,HO2HC = X

%6818

2R

N. V. Ivanova, S. I. Sviridov,* S. V. Shorshnev, A. E. Stepanov

N N

1R

HS

N N

1R

A Convenient Synthesis of 4,5-Disubstituted 1,2,4-Triazoles Functionalized in Position 3

NC

E. R. Anabha, C. V. Asokan*

HN

1R

OHC

2RS

S2R

3lCOP

FMD

2RS

S2R

A Convenient Preparation of 2-Aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and Their Application in the Synthesis of 5-Aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles

2]

3OS3FC[

N + +

erutarepmet moor

2lC2HC

2OS3FC

rB

Unusually Facile Syntheses of Diquat (6,7-Dihydrodipyrido[1,2-a:2,1-c]pyrazinediium) and Related Cations

'"R

3R

L. Cai,* C. Brouwer, K. Sinclair, J. Cuevas, V. W. Pike

R N

'R

R"

evaworcim

4lCiT

2HN

'"R

"R

+ X X

'R

2R N

1R

Titanium(IV) Chloride Promoted Syntheses of New Imidazo[1,2-a]pyridine Derivatives under Microwave Conditions

1R

2R

HO

1R

C3F C 87 ot C 001

C3F

ro

1R

2tEO3FB

1R

ro

iL

3FC

O2tE C 001

iLuB-n

rB

3FC

1-(Trifluoromethyl)vinylation via Oxirane or Oxetane Ring-Opening: A Facile Synthesis of 4- or 5-Hydroxy-Functionalized 2-Trifluoromethyl-1-alkenes

%8939 :noisrevnoC

Q.-b. Song,* R.-x. Lin, M.-y. Teng, J. Zhang, C.-a. Ma

Papers

rA F F

O cF , F F

2)HO(BrA

h 1 ,xulfer HOeM ,F F F

,)0(dP rB

= rA ,lynecorref = cF

O cF

An Improved SuzukiMiyaura Cross-Coupling Reaction for the Synthesis of Fluorine-Substituted 3-Biaryl-1-ferrocenyl-2-propen-1-one

Table of Contents

161

Papers

166

Feature Article

182
FN4uB-n ot tnelaviuqe citehtnyS :"F" XgMhP ro iLhP ot tnelaviuqe citehtnyS :"hP" F hP hP nS hP F

M. Gingras,* Y. M. Chabre, J.-M. Raimundo

Book Review
Microwave Assisted Organic Synthesis Edited by J. P. Thierney and P. Lidstrm Reviewed by J. Carlos Menndez 186

Forthcoming Articles Instructions for Authors

N4uB-n

Tetrabutylammonium Difluorotriphenylstannate [Bu4N][Ph3SnF2]: Delivering Carbon or Fluorine Ligands via Hypercoordination

PSP

nipreluacoruF

OcA

nilahpecopihrordyhiD

cAO

OcA

L. Commeiras, J. Bourdron, S. Douillard, P. Barbier, N. Vanthuyne, V. Peyrot,* J.-L. Parrain*

OcA

OcA

A lailofixaT

enynepreluaC

cAO

OcA

OcA

Total Synthesis of Terpenoids Isolated from Caulerpale Algae and Their Inhibition of Tubulin Assembly

XIII XIV

eMO

HO

%77

OcA

eMO

HO

O OH

C. D. Heidecke, T. K. Lindhorst*

HO

OH O

d 3 ,eneulot ,IABT ,edimilahthp lyporpomorb-3 .2 h 2 ,xulfer ,HOeM ,OnS2uB .1

HO

OH

Regioselective Phthalimidopropyl-Modification of Carbohydrates in One Step

Table of Contents

XI

Author Index
Abeijon, P. 73 AL-Saleh, B. 59 Anabha, E. R. 151 Ando, H. 31 Asokan, C. V. 151 Barbier, P. 166 Batra, S. 63 Blanco, J. M. 73 Blum, J. 111 Bonauer, C. 1 Borodkin, G. S. 97 Bouillon, J.-P. 103 Bourdron, J. 166 Brouwer, C. 133 Brul, C. 103 Caamao, O. 73 Cai, L. 133 Chabre, Y. M. 182 Coe, B. J. 146 Commeiras, L. 166 Corbel, B. 81 Couthon-Gourvs, H. 81 Cuevas, J. 133 Curati, N. R. M. 146 Deshmukh, A. R. A. S. 115 Devipriya, S. 107 Dhanya, R. 107 Douillard, S. 166 Elnagdi, M. H. 59 Fernndez, F. 73 Fitzgerald, E. C. 146 Garca, M. D. 73 Gingras, M. 182 Gumaste, V. K. 115 Haelters, J. P. 81 Hassaneen, H. M. E. 59 Heidecke, C. D. 161 Horne, D. A. 49 Ichikawa, J. 128 Ishihara, H. 31 Ivanova, N. V. 156 Kogami, M. 31 Koketsu, M. 31 Knig, B. 1 Krishna, P. R. 55 Kumar, A. 21 Lakshmi, P. S. 55 Lin, R.-x. 123 Lindhorst, T. K. 161 Ma, C.-a. 123 Makhseed, S. 59 Miyake, F. Y. 49 Molander, G. A. 111 Nadano, R. 128 Nair, V. 107 Nicola, E. 103 Ozeryanskii, V. A. 97 Parrain, J.-L. 166 Peyrot, V. 166 Pietruszka, J. 24 Pike, V. W. 133 Pittman, C. U. Jr. 37 Portella, C. 103 Prakash, O. 21 Raimundo, J.-M. 182 Reddy, K. L. 55 Rupprecht, D. 89 Sadana, A. K. 21 Schmuck, C. 89 Schne, N. 24 Sharma, G. V. M. 55 Shenglof, M. 111 Shorshnev, S. V. 156 Simon, G. 81 Sinclair, K. 133 Singh, S. P. 21 Singh, V. 63 Song, Q.-b. 123 Sorokin, V. I. 97 Stepanov, A. E. 156 Sviridov, S. I. 156 Teng, M.-y. 123 Tiwari, D. K. 115 Tonsiengsom, F. 49 Urban, C. 89 Vanthuyne, N. 166 Vidya, N. 107 Walden, N. 89 Walenzyk, T. 1 Yakushijin, K. 49 Zhang, J. 123 Zhou, A. 37